Pyridothiazines Having Herbicidal Action

ABSTRACT

Substituted pyridines of the formula I 
     
       
         
         
             
             
         
       
     
     in which the variables are defined according to the description, processes and intermediates for preparing the compounds of the formula I and their N-oxides, their agriculturally suitable salts, compositions comprising them and their use as herbicides, and also methods for controlling unwanted vegetation.

The present invention relates to substituted pyridines of the formula I

in which the variables have the following meaning:

-   R is O—R^(A), S(O)_(n)R^(A) or O—S(O)_(n)R^(A);    -   R^(A) is hydrogen, C₁-C₄-alkyl, Z—C₃-C₆-cycloalkyl,        C₂-C₆-alkenyl, Z—C₃-C₆-cycloalkenyl, C₂-C₆-alkynyl,        Z-(tri-C₁-C₄-alkyl)silyl, Z—C(═O)—R^(a),        Z—NR^(i)—C(O)—NR^(i)R^(ii), Z—P(═O)(R^(a))₂, NR^(i)R^(ii), a 3-        to 7-membered monocyclic or 9- or 10-membered bicyclic        saturated, unsaturated or aromatic heterocycle which contains 1,        2, 3 or 4 heteroatoms selected from the group consisting of O, N        and S and which may be partially or fully substituted by groups        R^(a) and/or R^(b),        -   R^(a) is hydrogen, OH, C₁-C₈-alkyl, C₁-C₄-haloalkyl,            Z—C₃-C₆-cycloalkyl, C₂-C₈-alkenyl, Z—C₅-C₆-cycloalkenyl,            C₂-C₈-alkynyl, Z—C₁-C₆-alkoxy, Z—C₁-C₄-haloalkoxy,            Z—C₃-C₈-alkenyloxy, Z—C₃-C₈-alkynyloxy, NR^(i)R^(ii),            C₁-C₆-alkylsulfonyl, Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl,            Z-phenoxy, Z-phenylamino or a 5- or 6-membered monocyclic or            9- or 10-membered bicyclic heterocycle which contains 1, 2,            3 or 4 heteroatoms selected from the group consisting of O,            N and S, where the cyclic groups are unsubstituted or            substituted by 1, 2, 3 or 4 groups R^(b);            -   R^(i), R^(ii) independently of one another are hydrogen,                C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₃-C₈-alkenyl,                C₃-C₈-alkynyl, Z—C₃-C₆-cycloalkyl, Z—C₁-C₈-alkoxy,                Z—C₁-C₈-haloalkoxy, Z—C(═O)—R^(a), Z-phenyl, a 3- to                7-membered monocyclic or 9- or 10-membered bicyclic                saturated, unsaturated or aromatic heterocycle which                contains 1, 2, 3 or 4 heteroatoms selected from the                group consisting of O, N and S and which is attached via                Z;            -   R^(i) and R^(ii) together with the nitrogen atom to                which they are attached may also form a 5- or 6-membered                monocyclic or 9- or 10-membered bicyclic heterocycle                which contains 1, 2, 3 or 4 heteroatoms selected from                the group consisting of O, N and S;        -   R^(b) independently of one another are Z—CN, Z—OH, Z—NO₂,            Z-halogen, oxo (═O), ═N—R^(a), C₁-C₈-alkyl, C₁-C₄-haloalkyl,            C₂-C₈-alkenyl, C₂-C₈-alkynyl, Z—C₁-C₈-alkoxy,            Z—C₁-C₈-haloalkoxy, Z—C₃-C₁₀-cycloalkyl,            O—Z—C₃-C₁₀-cycloalkyl, Z—C(═O)—R^(a), NR^(i)R^(ii), Z-(tri            C₁-C₄ alkyl)silyl, Z-phenyl and S(O)_(n)R^(bb); two groups            R^(b) may together form a ring which has three to six ring            members and, in addition to carbon atoms, may also contain            heteroatoms from the group consisting of O, N and S and may            be unsubstituted or substituted by further groups R^(b);            -   R^(bb) is C₁-C₈-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,                C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl or C₁-C₆-haloalkyl;        -   Z is a covalent bond or C₁-C₄-alkylene;    -   n is 0, 1 or 2;-   R¹ is cyano, halogen, nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₁-C₆-haloalkyl, Z—C₁-C₆-alkoxy,    Z—C₁-C₄-alkoxy-C₁-C₄-alkoxy, Z—C₁-C₄-alkylthio,    Z—C₁-C₄-alkylthio-C₁-C₄-alkylthio, C₂-C₆-alkenyloxy,    C₂-C₆-alkynyloxy, C₁-C₆-halo-alkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy,    S(O)_(n)R^(bb), Z-phenoxy, Z-heterocyclyloxy, where heterocyclyl is    a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic    saturated, partially unsaturated or aromatic heterocycle which    contains 1, 2, 3 or 4 heteroatoms selected from the group consisting    of O, N and S, where cyclic groups are unsubstituted or partially or    fully substituted by R^(b);-   A is N or C—R²;-   R², R³, R⁴, R⁵ independently of one another are hydrogen, Z-halogen,    Z—CN, Z—OH, Z—NO₂, C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₂-C₈-alkenyl,    C₂-C₈-alkynyl, C₂-C₈-halo-alkenyl, C₂-C₈-haloalkynyl,    Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy, Z—C₁-C₄-alkoxy-C₁-C₄-alkoxy,    Z—C₁-C₄-alkylthio, Z—C₁-C₄-alkylthio-C₁-C₄-alkylthio, Z—C₁-C₆-halo    alkylthio, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy,    C₁-C₄-halo-alkoxy-C₁-C₄-alkoxy, Z—C₃-C₁₀-cycloalkyl,    O—Z—C₃-C₁₀-cycloalkyl, Z—C(═O)—R^(a), NR^(i)R^(ii),    Z-(tri-C₁-C₄-alkyl)silyl, S(O)_(n)R^(bb), Z-phenyl, Z¹-phenyl,    Z-heterocyclyl, Z¹-heterocyclyl, where heterocyclyl is a 5- or    6-membered monocyclic or 9- or 10-membered bicyclic saturated,    partially unsaturated or aromatic heterocycle which contains 1, 2, 3    or 4 heteroatoms selected from the group consisting of O, N and S,    where cyclic groups are unsubstituted or partially or fully    substituted by R^(b);-   R² together with the group attached to the adjacent carbon atom may    also form a five- to ten-membered saturated or partially or fully    unsaturated mono- or bicyclic ring which, in addition to carbon    atoms, may contain 1, 2 or 3 heteroatoms selected from the group    consisting of O, N and S and may be substituted by further groups    R^(b);    -   Z¹ is a covalent bond, C₁-C₄-alkyleneoxy, C₁-C₄-oxyalkylene or        C₁-C₄-alkyleneoxy-C₁-C₄-alkylene;-   R⁶ is hydrogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-haloalkylthio;-   R⁷, R⁸ independently of one another are hydrogen, halogen or    C₁-C₄-alkyl;-   R^(x) is C₁-C₆-alkyl, C₁-C₄-haloalkyl, C₁-C₂-alkoxy-C₁-C₂-alkyl,    C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl    or Z-phenyl, which is unsubstituted or substituted by 1 to 5 groups    R^(b);    where in the groups R^(A), and R¹, R², R³, R⁴ and R⁵ and their    subsubstituents, the carbon chains and/or the cyclic groups may be    partially or fully substituted by groups R^(b),    or an N-oxide or an agriculturally suitable salt thereof.

Moreover, the invention relates to processes and intermediates forpreparing the pyridazines of the formula I and the N-oxides thereof, theagriculturally usable salts thereof, and also to active compoundcombinations comprising them, to compositions comprising them and totheir use as herbicides, i.e. for controlling harmful plants, and alsoto a method for controlling unwanted vegetation which comprises allowinga herbicidally effective amount of at least one pyridazine compound ofthe formula I or of an agriculturally suitable salt of I to act onplants, their seed and/or their habitat.

Further embodiments of the present invention can be found in the claims,the description and the examples. It is to be understood that thefeatures mentioned above and those still to be illustrated below of thesubject matter of the invention can be applied not only in therespective given combination but also in other combinations withoutleaving the scope of the invention.

WO 2008/063180, and WO 2010/029311 describe herbicidal pyridopyrazines;however, their herbicidal action at low application rates and/or theircompatibility with crop plants leave scope for improvement.

It is an object of the present invention to provide compounds havingherbicidal action. To be provided are in particular active compoundshaving strong herbicidal action, in particular even at low applicationrates, whose compatibility with crop plants is sufficient for commercialapplication.

These and further objects are achieved by the compounds of the formula Idefined at the outset and by their N-oxides and also theiragriculturally suitable salts.

The compounds according to the invention can be prepared analogously tothe synthesis routes described in the abovementioned documents accordingto standard processes of organic chemistry, for example according to thefollowing synthesis route:

Pyridazinecarboxylic acids of the formula II can be reacted withcarbonyl compounds of the formula III to give compounds of the formulaIV. In the formulae II and III, the variables have the meaning given forformula I. The group Hal is a halogen atom or another suitablenucleophilic leaving group, such as alkoxy or phenoxy.

This reaction is usually carried out at temperatures of from −78° C. to120° C., preferably from −20° C. to 50° C., in an inert organic solventin the presence of a base, such as, for example, triethylamine (cf. J.Agric. and Food Chem. 1994, 42(4), 1019-1025), a catalyst, such as, forexample, dicyclohexylcarbodiimide (cf. Egyptian Journal of Chemistry1994, 37(3), 273-282) or other known coupling agents.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene,o-, m- and p-xylene, halogenated hydrocarbons, such as methylenechloride, chloroform and chloro-benzene, ethers, such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran (THF), nitriles, such as acetonitrile and propionitrile,ketones, such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, and also dimethyl sulfoxide, dimethylformamide(DMF) and dimethylacetamide, particularly preferably halogenatedhydrocarbons, such as methylene chloride, chloroform and chlorobenzene.It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as lithiumoxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal andalkaline earth metal hydrides, such as lithium hydride, sodium hydride,potassium hydride and calcium hydride, alkali metal and alkaline earthmetal carbonates, such as lithium carbonate, potassium carbonate andcalcium carbonate, and also alkali metal bicarbonates, such as sodiumbicarbonate, organometallic compounds, in particular alkali metalalkyls, such as methyllithium, butyllithium and phenyllithium,alkylmagnesium halides, such as methylmagnesium chloride, and alsoalkali metal and alkaline earth metal alkoxides, such as sodiummethoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxideand dimethoxymagnesium, moreover organic bases, for example tertiaryamines, such as trimethylamine, triethylamine, tributylamine,diisopropylethylamine and N-methylpiperidine, pyridine, substitutedpyridines, such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Particular preference is given to tertiary aminessuch as trimethylamine, triethylamine, tributylamine,diisopropyl-ethylamine and alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate and calciumcarbonate. The bases are generally employed in equimolar amounts;however, they can also be used in catalytic amounts, in excess or, ifappropriate, as solvents.

The starting materials are generally reacted with one another inequimolar amounts.

The compounds of the formula IV are activated by introducing a leavinggroup L¹. Suitable leaving groups L¹ are, in general, groups whichincrease the electrophilicity of the carbonyl group, for exampleO-alkyl, O-aryl, halides, activated esters or aldehydes (such as, forexample, Weinreb amide), in particular pentafluorophenoxy.

This reaction is usually carried out at temperatures of from −78° C. to120° C., preferably from −20° C. to 50° C., in an inert organic solventin the presence of a base, such as, for example, triethylamine (cf. J.Agric. and Food Chem. 1994, 42(4), 1019-1025), a catalyst, such as, forexample, dicyclohexylcarbodiimide (cf. Egyptian Journal of Chemistry1994, 37(3), 273-282) or other known coupling agents.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene,o-, m- and p-xylene, halogenated hydrocarbons, such as methylenechloride, chloroform and chlorobenzene, ethers, such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles, such as acetonitrile and propionitrile,ketones, such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, and also dimethyl sulfoxide, dimethylformamideand dimethylacetamide, particularly preferably methylene chloride andtoluene. It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal oxides, such as lithium oxide, sodiumoxide, calcium oxide and magnesium oxide, alkali metal and alkalineearth metal hydrides, such as lithium hydride, sodium hydride, potassiumhydride and calcium hydride, alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal bicarbonates, such as sodiumbicarbonate, organometallic compounds, in particular alkali metalalkyls, such as methyllithium, butyllithium and phenyllithium,alkylmagnesium halides, such as methylmagnesium chloride, and alsoalkali metal and alkaline earth metal alkoxides, such as sodiummethoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxideand dimethoxymagnesium, moreover organic bases, for example tertiaryamines, such as trimethylamine, triethylamine, tributylamine,diisopropylethylamine and N-methyl-piperidine, pyridine, substitutedpyridines, such as collidine, lutidine and 4-dimethyl-aminopyridine, andalso bicyclic amines. Particular preference is given to alkali metal andalkaline earth metal carbonates, such as lithium carbonate, potassiumcarbonate, calcium carbonate, cesium carbonate and rubidium carbonate.The bases are generally employed in catalytic amounts; however, they canalso be used in equimolar amounts, in excess or, if appropriate, assolvents.

The starting materials are generally reacted with one another inequimolar amounts.

Suitable agents H-L¹ are alcohols, optionally subst. phenols,N,O-dialkylhydroxyl-amine, in particular pentafluorophenol orN,O-dimethylhydroxylamine.

The compounds of the formula V are cyclized to give the compounds of theformula I.

This reaction is usually carried out at temperatures of from −78° C. to120° C., preferably from −20° C. to 50° C., in an inert organic solventin the presence of a base or a Lewis acid or a catalyst [cf. Silverman,Richard B. J. Am. Chem. Soc. 1981, 103(13), 3910].

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene,o-, m- and p-xylene, halogenated hydrocarbons, such as methylenechloride, chloroform and chloro-benzene, ethers, such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles, such as acetonitrile and propionitrile,ketones, such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, and also dimethyl sulfoxide, dimethylformamideand dimethylacetamide, particularly preferably acetonitrile anddimethylformamide. It is also possible to use mixtures of the solventsmentioned.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal oxides, such as lithium oxide, sodiumoxide, calcium oxide and magnesium oxide, alkali metal and alkalineearth metal hydrides, such as lithium hydride, sodium hydride, potassiumhydride and calcium hydride, alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate, calciumcarbonate, cesium carbonate and rubidium carbonate, and also alkalimetal bicarbonates, such as sodium bicarbonate, organometalliccompounds, in particular alkali metal alkyls, such as methyllithium,butyllithium and phenyllithium, alkyl-magnesium halides, such asmethylmagnesium chloride, and also alkali metal and alkaline earth metalalkoxides, such as sodium methoxide, sodium ethoxide, potassiumethoxide, potassium tert-butoxide and dimethoxymagnesium, moreoverorganic bases, for example tertiary amines, such as trimethylamine,triethylamine, tributylamine, diisopropylethylamine andN-methylpiperidine, pyridine, substituted pyridines, such as collidine,lutidine and 4-dimethylaminopyridine, and also bicyclic amines.Particular preference is given to alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate, calciumcarbonate, cesium carbonate and rubidium carbonate.

The bases are generally employed in catalytic amounts; however, they canalso be used in equimolar amounts, in excess or, if appropriate, assolvents.

The starting materials are generally reacted with one another inequimolar amounts.

Alternatively, the compounds of the formula I can also be obtained via areverse reaction sequence, i.e. the reaction of the compounds of theformula II with compounds H-L¹ gives the activated derivatives of theformula VI.

Per se, this reaction is carried out under the conditions mentioned forthe reaction of the formula IV with H-L¹.

The compounds of the formula VI can then be reacted with compounds IIIto give the derivatives of the formula V.

Per se, this reaction is carried out under the conditions mentioned forthe reaction of the formula II with III.

The phenylacetic acid derivatives of the formula III are known or can beprepared from correspondingly substituted benzoic acids or halobenzeneson the basis of syntheses known in the literature [cf. Journal ofMedicinal Chemistry 49(12), 3563-3580 (2006); Journal of MedicinalChemistry 28(10), 1533-6 (1985); US 2004/077901; US 2004/068141;Chemistry-A European Journal 14(26), 7969-7977 (2008); Journal of EnzymeInhibition and Medicinal Chemistry 17(3), 187-196 (2002)]. Suitablysubstituted benzoic acids and halobenzenes are known, for example from:WO 2002/006211, WO 2009/058237, WO 98/52926, WO 96/26193, EP-A 352 543,WO 98/52926, WO 97/30986, WO 98/12180.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separating the phases and, if appropriate,chromatographic purification of the crude products. Some of theintermediates and end products are obtained in the form of colorless orslightly brownish viscous oils which are purified or freed from volatilecomponents under reduced pressure and at moderately elevatedtemperature. If the intermediates and end products are obtained assolids, the purification can also be carried out by recrystallization ordigestion.

If individual compounds I cannot be obtained by the routes describedabove, they can be prepared by derivatization of other compounds I.

If the synthesis yields mixtures of isomers, a separation is generallyhowever not necessarily required since in some cases the individualisomers can be interconverted during work-up for use or duringapplication (for example under the action of light, acids or bases).Such conversions may also take place after application, for example inthe case of the treatment of plants in the treated plant or in theharmful plant to be controlled.

The organic moieties mentioned for the substituents of the compoundsaccording to the invention are collective terms for individualenumerations of the individual group members. All hydrocarbon chains,such as alkyl, haloalkyl, alkenyl, alkynyl, and the alkyl moieties andalkenyl moieties in alkoxy, haloalkoxy, alkylamino, dialkylamino,N-alkylsulfonylamino, alkenyloxy, alkynyloxy, alkoxyamino,alkylaminosulfonylamino, dialkylaminosulfonylamino, alkenylamino,alkynylamino, N-(alkenyl)-N-(alkyl)amino, N-(alkynyl)-N-(alkyl)amino,N-(alkoxy)-N-(alkyl)amino, N-(alkenyl)-N-(alkoxy)amino orN-(alkynyl)-N-(alkoxy)amino can be straight-chain or branched.

The prefix C_(n)-C_(m)- indicates the respective number of carbons ofthe hydrocarbon unit. Unless indicated otherwise, halogenatedsubstituents preferably carry one to five identical or different halogenatoms, in particular fluorine atoms or chlorine atoms.

The meaning halogen denotes in each case fluorine, chlorine, bromine oriodine.

Examples of other meanings are:

alkyl and the alkyl moieties for example in alkoxy, alkylamino,dialkylamino: saturated straight-chain or branched hydrocarbon radicalshaving one or more carbon atoms, for example 1 or 2, 1 to 4 or 1 to 6carbon atoms, for example C₁-C₆-alkyl, such as methyl, ethyl, propyl,1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl,pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl. In one embodimentaccording to the invention, alkyl denotes small alkyl groups, such asC₁-C₄-alkyl. In another embodiment according to the invention, alkyldenotes relatively large alkyl groups, such as C₅-C₆-alkyl.

Haloalkyl: an alkyl radical as mentioned above, some or all of whosehydrogen atoms are substituted by halogen atoms, such as fluorine,chlorine, bromine and/or iodine, for example chloromethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoro-methyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl,2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoro-ethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl,2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl,3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl,2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyland nonafluorobutyl.

Cycloalkyl and the cycloalkyl moieties for example in cycloalkoxy orcycloalkyl-carbonyl: monocyclic saturated hydrocarbon groups havingthree or more carbon atoms, for example 3 to 6 carbon ring members, suchas cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Alkenyl and the alkenyl moieties for example in alkenyloxy:monounsaturated straight-chain or branched hydrocarbon radicals havingtwo or more carbon atoms, for example 2 to 4, 2 to 6 or 3 to 6 carbonatoms, and a double bond in any position, for example C₂-C₆-alkenyl,such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl,2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl,3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl.

Cycloalkenyl: monocyclic monounsaturated hydrocarbon groups having 3 to6, preferably 5 or 6, carbon ring members, such as cyclopenten-1-yl,cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl.

Alkynyl and the alkynyl moieties for example in alkynyloxy,alkynylamino: straight-chain or branched hydrocarbon groups having twoor more carbon atoms, for example 2 to 4, 2 to 6 or 3 to 6 carbon atoms,and a triple bond in any position, for example C₂-C₆-alkynyl, such asethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl,1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl,1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl,3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl,3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl,1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl,1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl.

Alkoxy: alkyl as defined above which is attached via an oxygen atom, forexample methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy,1-methylpropoxy, 2-methyl-propoxy or 1,1-dimethylethoxy, pentoxy,1-methylbutoxy, 2-methylbutoxy, 3-methyl-butoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethyl-propoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methyl-pentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethyl-butoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy.

3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated,unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4heteroatoms selected from the group consisting of O, N and S and may beattached via carbon or nitrogen. From among these, preference is givento 5- or 6-membered heterocycles.

Saturated or unsaturated heterocyclic groups which are attached vianitrogen or carbon, such as: pyridazin-3-yl, pyridazin-4-yl,pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl,isoxazolin-3-yl, isoxazolin-4-yl, isoxazolin-5-yl, isothiazol-3-yl,isothiazol-4-yl, isothiazol-5-yl, imidazol-1-yl, imidazol-2-yl,imidazol-4-yl, oxazol-2-yl, oxazolin-2-yl, thiazolin-2-yl andmorpholinyl.

Heteroaromatic groups which are attached via nitrogen or carbon, suchas: pyrazol-3-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrazol-1-yl,pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl,imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl,thiazol-4-yl, thiazol-5-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl,pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-4-yl,pyrazin-2-yl, [1H]-tetrazol-5-yl and [2H]-tetrazol-5-yl.

The compounds of the formula I may, depending on the substitutionpattern, contain one or more further centers of chirality. Accordingly,the compounds according to the invention can be present as pureenantiomers or diastereomers or as enantiomer or diastereomer mixtures.The invention provides both the pure enantiomers or diastereomers andtheir mixtures.

The compounds of the formula I may also be present in the form of theN-oxides and/or of their agriculturally useful salts, the type of saltgenerally not being important. Suitable salts are generally the salts ofthose cations or the acid addition salts of those acids whose cationsand anions, respectively, have no adverse effect on the herbicidalactivity of the compounds I.

Suitable cations are in particular ions of the alkali metals, preferablylithium, sodium or potassium, of the alkaline earth metals, preferablycalcium or magnesium, and of the transition metals, preferablymanganese, copper, zinc or iron. Another cation that may be used isammonium, where, if desired, one to four hydrogen atoms may be replacedby C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,dimethylammonium, diisopropyl-ammonium, tetramethylammonium,tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium,di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium. Another suitableammonium cation is the pyridine nitrogen atom of the formula Iquaternized by alkylation or arylation. Also suitable are phosphoniumions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, orsulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of suitable acid addition salts are primarily chloride, bromide,fluoride, hydrogensulfate, sulfate, dihydrogenphosphate,hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and also the anions of C₁-C₄-alkanoicacids, preferably formate, acetate, propionate, butyrate ortrifluoroacetate.

With respect to the variables, the particularly preferred embodiments ofthe intermediates correspond to those of the groups of the formula I.

In a particular embodiment, the variables of the compounds of theformula I have the following meanings, these meanings, both on their ownand in combination with one another, being particular embodiments of thecompounds of the formula I:

In one preferred embodiment of the compounds of the formula I, R isO—R^(A), in which R^(A) is H, C₃-C₈-alkenyl, C₃-C₈-haloalkenyl,C₃-C₈-alkynyl, C₃-C₈-haloalkynyl, C₁-C₆-alkylcarbonyl, such as C(O)CH₃,C(O)CH₂CH₃, C(O)CH(CH₃)₂ or C(O)C(CH₃)₃; C₁-C₆-cycloalkylcarbonyl, suchas cyclopropylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl;C₂-C₆-alkenylcarbonyl, such as C(O)CH═CH₂ or C(O)CH₂CH═CH₂, optionallysubst. benzoyl, such as C(O)C₆H₅, C(O)[2-CH₃—C₆H₄], C(O)[4-CH₃—C₆H₄],C(O)[2-F—C₆H₄], C(O)[4-F—C₆H₄], or optionally subst. heteroaryl, such aspyridyl, which is attached via a carbonyl group. Particularlypreferably, R^(A) is H, C₃-C₄-alkenyl, C₃-C₄-alkynyl orC₁-C₆-alkylcarbonyl. Especially preferably, R^(A) is selected from thegroup consisting of H, CH₂CH═CH₂, CH₂C≡CH, CH₃, C(O)CH₃, C(O)CH₂CH₃,C(O)CH(CH₃)₂, C(O)C(CH₃)₃, C(O)-c-C₃H₅, C(O)—C₆H₅, C(O)—CH₂C₆H₅,C(O)CH₂Cl, C(O)CF₃, C(O)CH₂OCH₃, C(O)N(CH₃)₂ and C(O)OCH₂CH₃.

In a further preferred embodiment of the compounds of the formula I, Ris OS(O)_(n)—R^(A) where n is preferably 0 or 2, in particular 2, suchas, for example, OS(O)₂—CH₃, OS(O)₂—C₂H₅, OS(O)₂—C₃H₇, OS(O)₂—C₆H₅ orOS(O)₂-(4-CH₃—C₆H₄).

In a further preferred embodiment, R is O—S(O)_(n)—NR^(i)R^(ii), inparticular with the groups NR^(i)R^(ii) mentioned below as preferred.

R^(i) and R^(ii) are preferably C₁-C₈-alkyl, C₁-C₄-haloalkyl,Z—C₃-C₆-cycloalkyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy, Z-phenyl,Z—C(═O)—R^(a) or Z-hetaryl. Preference is given here to CH₃, C₂H₅,n-propyl, CH(CH₃)₂, butyl, 2-chloroethyl, cyclopentyl, cyclohexyl,2-ethoxymethyl, 2-chloroethoxy, phenyl, pyrimidines or triazines, whichrings are unsubstituted or substituted. Preferred substituents areC₁-C₄-alkylcarbonyl or C₁-C₄-haloalkylcarbonyl, in particular C(═O)—CH₃,C(═O)—C₂H₅, C(═O)—C₃H₇, C(═O)—CH(CH₃)₂, butylcarbonyl and C(═O)—CH₂Cl.Particularly preferred aspects of group NR^(i)R^(ii) areN(di-C₁-C₄-alkyl), in particular N(CH₃)—C₁-C₄-alkyl, such as N(CH₃)₂,N(CH₃)CH₂CH₃, N(CH₃)C₃H₇ and N(CH₃)CH(CH₃)₂.

Further particularly preferred aspects of NR^(i)R^(ii) are NH-aryl,where aryl is preferably phenyl which is substituted—in particular inthe 2- and 6-position—by one to three identical or different groups fromthe group consisting of halogen, CH₃, halo-C₁-C₂-alkyl,halo-C₁-C₂-alkoxy and carboxyl, such as 2-Cl, 6-COOH—C₆H₃, 2,6-Cl₂-C₆H₃,2,6-F₂—C₆H₃, 2,6-Cl₂ 3-C₆H₂, 2-CF₃, 6-CH₂CHF₂—C₆H₃, 2-CF₃, 6-OCF₃—C₆H₃and 2-CF₃, 6-CH₂CHF₂—C₆H₃.

In a further preferred embodiment of the invention, R^(A) is a 5- or6-membered heterocycle optionally substituted by R^(b) as defined above,which preferably has either 1, 2, 3 or 4 N or 1 O or 1 S atom and ifappropriate 1 or 2 N atoms as ring members and which is unsubstituted ormay have 1 or 2 substituents selected from R^(b). Preference is given tosaturated or unsaturated groups attached via nitrogen, such as, forexample:

Heteroaromatic groups: pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl,pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 2-furyl, 3-furyl,2-thienyl, 3-thienyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl,isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl,isothiazol-4-yl, isothiazol-5-yl, imidazol-1-yl, imidazol-2-yl,imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl,thiazol-4-yl and thiazol-5-yl.

In another aspect, R^(A) is a heteroaromatic group attached via carbon,such as pyrazol-3-yl, imidazol-5-yl, oxazol-2-yl, thiazol-2-yl,thiazol-4-yl, thiazol-5-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl,pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-4-yl,pyrazin-2-yl, [1H]-tetrazol-5-yl and [2H]-tetrazol-5-yl, where each ofthe heterocycles mentioned here in an exemplary manner may have 1 or 2substituents selected from R^(b). Preferred groups R^(b) are in thiscase in particular F, Cl, CN, NO₂, CH₃, C₂H₅, OCH₃, OC₂H₅, OCHF₂, OCF₃and CF₃.

In particularly preferred embodiments of the compounds of the formula I,R is selected from the group consisting of OH, OCH₂CH═CH₂, OCH₂C≡CH,OCH₃, OC(O)CH₃, OC(O)CH₂CH₃, OC(O)CH(CH₃)₂, OC(O)C(CH₃)₃, OC(O)-c-C₃H₅,OC(O)—C₆H₅, OC(O)—CH₂C₆H₅, OC(O)CH₂Cl, OC(O)—CF₃, OC(O)—CH₂OCH₃,OC(O)—N(CH₃)₂ and OC(O)—OCH₂CH₃.

Groups R^(a) preferred for the compounds of the formula I are selectedfrom the group consisting of OH, C₁-C₈-alkyl, C₃-C₈-alkenyl,C₃-C₈-alkynyl, Z—C₁-C₆-alkoxy, Z—C₁-C₄-haloalkoxy, Z—C₃-C₈-alkenyloxy,Z—C₃-C₈-alkynyloxy and NR^(i)R^(ii).

For the compounds of the formula I, the groups R^(b) are preferablyselected from the group consisting of halogen, oxo (═O), ═N—R^(a),C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,Z—C₁-C₄-haloalkoxy, C₁-C₄-alkoxy, C₁-C₄-alkyl,C₁-C₄-alkylthio-C₁-C₄-alkyl, Z—C(═O)—R^(a) and S(O)_(n)R^(bb), whereR^(bb) is preferably C₁-C₄-alkyl or C₁-C₄-haloalkyl and n is 0, 1 or 2.

Particularly preferably, R^(b) is a group selected from the groupconsisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-alkylthio, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy,C₁-C₄-haloalkylthio, C₃-C₄-alkenyl, C₃-C₄-alkynyl and ═N—C₁-C₄-alkoxy.

Two groups R^(b) together may form a ring which preferably has three toseven ring members and, in addition to carbon atoms, may also containheteroatoms from the group consisting of O, N and S and which may beunsubstituted or substituted by further groups R^(b). These substituentsR^(b) are preferably selected from the group consisting of halogen,C₁-C₄-alkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl.

Groups R^(a) and R^(b) are selected independently of one another if aplurality of such groups is present.

In a preferred embodiment of the compounds of the formula I, R¹ iscyano, halogen, nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-haloalkyl, Z—C₁-C₆-alkoxy, Z—C₁-C₄-alkoxy-C₁-C₄-alkoxy,Z—C₁-C₄-alkylthio, Z—C₁-C₄-alkylthio-C₁-C₄-alkylthio, C₂-C₆-alkenyloxy,C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy,S(O)_(n)R^(bb), Z-phenoxy, Z-heterocyclyloxy, where heterocyclyl is a 5-or 6-membered monocyclic or 9- or 10-membered bicyclic saturated,partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or4 heteroatoms selected from the group consisting of O, N and S, cyclicgroups being unsubstituted or partially or fully substituted by R^(b).

In a particularly preferred embodiment of the compounds of the formulaI, R¹ is halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy-C₁-C₄*alkyl, C₁-C₄-alkoxy C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkylthio-C₁-C₄-alkyl,C₁-C₄-alkylthio-C₁-C₄-alkyl-thio-C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy,C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy,S(O)_(n)—C₁-C₄-alkyl and S(O)_(n)—C₁-C₄-haloalkyl. Particularlypreferably, R¹ is selected from the group consisting of F, Cl, Br, NO₂,CH₃, CF₃, OCH₃, OCF₃, SCF₃, SO₂CH₃, OCH₂CH₂OCH₃, CH₂OCH₂CH₂OCH₃,CH₂OCH₂CF₃.

In a further preferred embodiment of the compounds of the formula I, Ais C—R². These compounds correspond to the formula I.1

where the variables have the meanings defined at the outset andpreferably the meanings mentioned as preferred.

Particularly preferably, in the compounds of the formula I.1, the group

-   R¹ is halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy C₁-C₄-alkoxy C₁-C₄-alkyl,    C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio    or C₁-C₄-alkylsulfonyl, in particular F, Cl, Br, I, NO₂, CH₃, CF₃,    OCH₃, OCF₃, OCHF₂, SCF₃, SCHF₂, SO₂CH₃, CH₂OCH₂CH₂OCH₃;-   R³ is H, halogen, CN, NO₂, C₁-C₄-alkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulfonyl, in particular H, F, Cl, Br, CN, NO₂, CH₃,    CH₂CH₃, CF₃, CHF₂, OCH₃, OCF₃, OCHF₂, SCH₃, SO₂CH₃ or SO₂CH₂CH₃;-   R⁴, R⁵ are independently selected from the group consisting of H, F    and Cl.

Particularly preferably, in the compounds of the formula I.1, the group

-   R¹ is halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy    C₁-C₄-alkyl, C₁-C₄-alkoxy C₁-C₄-alkoxy C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio or    C₁-C₄-alkylsulfonyl, in particular F, Cl, Br, NO₂, CH₃, CF₃, OCH₃,    OCF₃, OCHF₂, SCF₃, SCHF₂, SO₂CH₃, CH₂OCH₂CH₂OCH₃;-   R³ is H, halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl, in particular H,    F, Cl, Br, CN, NO₂, CH₃, CH₂CH₃, CF₃, CHF₂, OCH₃, OCF₃, OCHF₂, SCH₃,    SO₂CH₃ or SO₂CH₂CH₃;-   R⁴ is H;-   R⁵ is H, F or Cl.

In a preferred embodiment of the compounds of the formula I.1, R² isZ¹-heterocyclyl where heterocyclyl is a 5- or 6-membered monocyclic or9- or 10-membered bicyclic, saturated, partially unsaturated or aromaticheterocycle which contains 1, 2, 3 or 4 heteroatoms selected from thegroup consisting of O, N and S, cyclic groups being unsubstituted orpartially or fully substituted by R^(b).

R² is in this case preferably a 3- to 7-membered monocyclic or 9- or10-membered bicyclic saturated, partially unsaturated or aromaticheterocycle which is attached via Z¹ and contains 1, 2, 3 or 4heteroatoms selected from the group consisting of O, N and S, where thecyclic groups are unsubstituted or partially or fully substituted bygroups R^(b).

In a further preferred aspect of the compounds of the formula I.1, R² isa 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated,partially unsaturated or aromatic heterocycle which is attached directlyor via C₁-C₄-alkyleneoxy, C₁-C₄-oxyalkylene orC₁-C₄-alkyleneoxy-C₁-C₄-alkylene, which contains 1, 2, 3 or 4heteroatoms selected from the group consisting of O, N and S and whichmay be substituted as defined at the outset.

A preferred aspect of group R² relates to five- or six-memberedsaturated or partially unsatured heterocycles, such as, for example,isoxazoline, tetrazolone, 1,2-dihydro-tetrazolone,1,4-dihydrotetrazolone, tetrahydrofuran, dioxolane, piperidine,morpholine and piperazine. Particular preference is given to3-isoxazoline, 5-isoxazoline, 1-tetrazolone, 2-tetrazolone,[1,3]dioxolane-2 and N-morpholine. Especially preferred are:4,5-dihydroisoxazole-3, unsubstituted or substituted by 5-CH₃, 5-CH₂F or5-CHF₂; 4,5-dihydroisoxazole-5, unsubstituted or substituted by 3-CH₃,3-OCH₃, 3-CH₂OCH₃, 3-CH₂SCH₃; 1-methyl-5-oxo-1,5-dihydrotetrazole-2;4-methyl-5-oxo-4,5-dihydro-tetrazole-1 and N-morpholine.

A further preferred aspect of group R² relates to five- or six-memberedaromatic heterocycles, such as, for example, isoxazole, pyrazole,thiazole, furyl, pyridine, pyrimidine and pyrazine. Particularpreference is given to 3-isoxazole, 5-isoxazole, 3-pyrazole, 5-pyrazole,2-thiazole, 2-oxazole, 2-furyl. Especially preferred are: 3-isoxazole,5-methyl-3-isoxazole, 5-isoxazole, 3-methyl-5-isoxazole,1-methyl-1H-pyrazole-3, 2-methyl-2H-pyrazole-3 and thiazole-2.

In a preferred aspect of the compounds of the formula I, the groupsR^(b) independently of one another are Z—CN, Z—OH, Z—NO₂, Z-halogen, oxo(═O), ═N—R^(a), C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₂-C₈-alkenyl,C₂-C₈-alkynyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy, Z—C₃-C₁₀-cycloalkyl,O—Z—C₃-C₁₀-cycloalkyl, Z—C(═O)—R^(a), NR^(i)R^(ii),Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl or S(O)_(n)R^(bb).

In a preferred aspect of heterocyclic groups R², the groups R^(b)independently of one another are preferably C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl.Especially preferred are CH₃, C₂H₅, CH₂F, CF₂H, CF₃, OCH₃, CH₂OCH₃,CH₂SCH₃, SCH₃ and SO₂CH₃.

The group R^(bb) is preferably C₁-C₈-alkyl.

In a preferred aspect, the group Z¹ is a covalent bond.

In a further preferred aspect, the group Z¹ is C₁-C₄-alkyleneoxy, inparticular OCH₂ or OCH₂CH₂.

In a further preferred aspect, the group Z¹ is C₁-C₄-oxyalkylene, inparticular CH₂O or CH₂CH₂O.

In a further preferred aspect, the group Z¹ isC₁-C₄-alkyleneoxy-C₁-C₄-alkylene, in particular OCH₂OCH₂ or OCH₂CH₂OCH₂.

Particularly preferred aspects of heterocycles attached via Z¹ includetetrahydro-furan-2-ylmethoxymethyl and [1,3]dioxolan-2-ylmethoxy.

In a further preferred embodiment of the compounds of the formula I.1,R² is phenyl which is attached via Z¹ or oxygen and is unsubstituted orsubstituted by C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl or C₁-C₄-alkoxy-C₁-C₄-alkoxy.

Particular preference is given in this case to a phenyl group which maybe partially or fully substituted—preferably mono-, di- ortrisubstituted, in particular monosubstituted—by groups R^(b). GroupsR^(b) preferred for this aspect include: C₁-C₂-alkyl, C₁-C₄-alkoxy,C₁-C₂-haloalkyl, C₁-C₂-alkoxy-C₁-C₂-alkyl or C₁-C₂-alkoxy-C₁-C₂-alkoxy.Particular preference is given to CH₃, C₂H₅, OCH₃, OC₂H₅, CHF₂, CF₃,OCHF₂, OCF₃, OCH₂OCH₃ and OCH₂CH₂OCH₃. Special preference is given toalkoxy, such as OCH₃ or OC₂H₅. A group R^(b) is preferably in position4. A particularly preferred phenyl group R² is a group P.

in which # denotes the bond via which the group R² is attached and thesubstituents are selected from R^(b) and are in particular:

R^(P2) H or F; R^(P3) H, F, Cl or OCH₃; and R^(P4) H, F, Cl, CH₃, CF₃,OCH₃, OCH₂OCH₃ or OCH₂CH₂OCH₃.

In a further preferred embodiment of the compounds of the formula I.1,R² is an aliphatic group selected from the group consisting ofC₁-C₈-alkyl, C₂-C₆-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₂-C₈-alkenyl,C₂-C₈-alkynyl, C₂-C₈-haloalkenyl, C₂-C₈-halo-alkynyl, C₁-C₆-alkoxy,Z—C₁-C₄-alkoxy-C₁-C₄-alkoxy, Z—C₁-C₄-haloalkoxy-C₁-C₄-alkoxy,Z—C₁-C₆-haloalkoxy, C₂-C₈-alkenyloxy, C₂-C₈-alkynyloxy,Z—C₁-C₄-alkylthio, Z—C₁-C₆-haloalkylthio, Z—C(═O)—R^(a) orS(O)_(n)R^(bb).

In a particularly preferred aspect of these compounds of the formulaI.1, R² is an aliphatic group selected from the group consisting ofC₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₂-C₄-alkoxy, C₁-C₄-haloalkoxy,C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-haloalkenyloxy,C₃-C₆-haloalkynyloxy, C₁-C₄-alkoxycarbonyl, S(O)₂—C₁-C₄-alkyl andS(O)₂—C₁-C₈-halo-alkyl.

Particularly preferred aliphatic groups R² include C₂-C₄-alkenyl,C₂-C₄-alkynyl, C₁-C₂-haloalkoxy-C₁-C₂-alkyl, C₃-C₄-alkenyloxy,C₃-C₄-alkynyloxy, C₁-C₄-alkylsulfonyl, C₁-C₄-alkoxy,C₁-C₄-alkoxycarbonyl and S(O)₂—C₁-C₄-alkyl. Special preference is givento CH═CH₂, CH═CHCH₃, CH₂OCH₂CF₃, OC₂H₅, OCH₂CH═CH₂, OCH₂C≡CH,OCH₂CH₂OCH₃, COOCH₃, COOC₂H₅ and SO₂CH₃, SO₂C₂H₅ and SO₂CH(CH₃)₂.

In a further preferred aspect, R² together with the group attached tothe adjacent carbon atom forms a five- to ten-membered saturated,partially or fully unsaturated mono- or bicyclic ring which, in additionto carbon atoms, may contain 1, 2 or 3 heteroatoms selected from thegroup consisting of O, N and S and which may be substituted by furthergroups R^(b).

In a particularly preferred aspect, R² together with R¹ or R³ forms afive- to ten-membered mono- or bicyclic, saturated or partiallyunsaturated ring which contains 1, 2, 3 or 4 heteroatoms selected fromthe group consisting of O, N and S and which may be partially or fullysubstituted by groups R^(b). Together with the phenyl group whichcarries the groups R¹ to R⁵, a nine- to fifteen-membered bi- ortricyclic, optionally heterocyclic, ring system results. Suitable are,for example, the following: 2,3-dihydrobenzo[b]thiophene 1,1-dioxide,thiochroman 1,1-dioxide, 2,3-dihydro-benzo[1,4]dithiin1,1,4,4-tetraoxide, 3H-benzothiazol-2-one, quinoline and saccharin.

Preferably, R² together with R¹ or R³ forms a five- or six-memberedmonocyclic, saturated or partially unsaturated ring.

Preferred bicyclic ring systems comprising the phenyl group attached tothe dioxodihydrothiatriazanaphthalene skeleton and R¹ and R² are, forexample, groups A to D:

# denotes the bond to the skeleton.

Preferred bi- and tricyclic ring systems comprising the phenyl groupattached to the dioxodihydrothiatriazanaphthalene skeleton and R² and R³contain one or two sulfur atoms and optionally one nitrogen atom.Preferred are groups E to L:

In groups A to L, the groups R^(b) independently of one another arepreferably halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio,C₁-C₄-haloalkoxy, C₁-C₄-haloalkylthio, C₃-C₄-alkenyl, C₃-C₄-alkynyl,═N—C₁-C₄-alkoxy.

The compounds of the formula I in which R² is one of groups A to Lcorrespond to the formulae I.A to I.L.

In the formulae I.A to I.L, R^(b) is preferably halogen, C₁-C₄-alkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkyl.

The following examples represent particularly preferred groups A to L:

-   R^(3A), R^(3B), R^(3C) and R^(3D) are preferably halogen,    C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, in particular F, Cl, Br,    CH₃, CF₃ or OCH₃.-   R^(bE1), R^(bE2) are preferably H, C₁-C₄-alkyl or C₁-C₄-alkoxy, in    particular R^(bE1) is H or CH₃; R^(bE2) is H, CH₃ or OCH₃.-   R^(bJ1) is preferably C₁-C₄-haloalkoxy, in particular OCH₂CH₂F.-   R^(bJ2) is preferably C₁-C₄-alkoxy, in particular OCH₃ or OCH₂CH₃.-   R^(bL) is preferably C₁-C₄-Alkyl or C₃-C₄-Alkenyl, in particular    CH₃, CH₂CH₃, CH₂CH₂CH₃, CH(CH₃)₂ or CH₂CH═CH₂.

In a further preferred embodiment of the compounds of the formula I, inparticular of the formula I.1, R³ is hydrogen, cyano, halogen, nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy orS(O)_(n)Rbb.

In a particularly preferred embodiment of the compounds of the formulaI, in particular of the formula I.1, R³ is hydrogen, halogen, CN, NO₂,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,S(O)_(n)—C₁-C₄-alkyl and S(O)_(n)—C₁-C₄-haloalkyl, where n is preferably0 or 2. Particularly preferably, R³ is selected from the groupconsisting of H, F, Cl, Br, CN, NO₂, CH₃, CF₃, CHF₂, OCH₃, OCF₃, OCHF₂,SCH₃, SCF₃, SCHF₂, SO₂CH₃, SO₂CH₂CH₃.

In further preferred aspects of the formula I.1, the groups R¹, R², R³,R⁴ and R⁵ together form the following substitution patterns: 2-Br, 2-Cl,2,4-Cl₂, 2-Cl-4-F, 2-Cl-5-F, 2-Cl-6-F, 2-Cl-4-CF₃, 2-Cl-5-CF₃,2-Cl-6-CF₃, 2-Cl-3,6-F₂, 2-F, 2,4-F₂, 2,5-F₂, 2,6-F₂, 2-F-4-CF₃,2-F-5-CF₃, 2-F-6-CF₃, 2,3,6-F₃, 2-NO₂, 2-NO₂-4-F, 2-NO₂-5-F, 2-NO₂-6-F,2-NO₂-4-CF₃, 2-NO₂-5-CF₃, 2-NO₂-6-CF₃, 2-NO₂-3,6-F₂, 2-CN, 2-CH₃,2-CH₃-4-F, 2-CH₃-5-F, 2-CH₃-6-F, 2-CH₃-4-CF₃, 2-CH₃-5-CF₃, 2-CH₃-6-CF₃,2-CH₃-3,6-F₂, 2-OCH₃, 2-OCH₃-4-F, 2-OCH₃-5-F, 2-OCH₃-6-F, 2-OCH₃-4-CF₃,2-OCH₃-5-CF₃, 2-OCH₃-6-CF₃, 2-OCH₃-3,6-F₂, 2-CHF₂, 2-CHF₂-4-F,2-CHF₂-5-F, 2-CHF₂-6-F, 2-CHF₂-4-CF₃, 2-CHF₂-5-CF₃, 2-CHF₂-6-CF₃,2-CHF₂-3,6-F₂, 2-CF₃, 2-CF₃-4-F, 2-CF₃-5-F, 2-CF₃-6-F, 2-CF₃-4-CF₃,2-CF₃-5-CF₃, 2-CF₃-6-CF₃, 2-CF₃-3,6-F₂, 2-OCHF₂, 2-OCHF₂-4-F,2-OCHF₂-5-F, 2-OCHF₂-6-F, 2-OCHF₂-4-CF₃, 2-OCHF₂-5-CF₃, 2-OCHF₂-6-CF₃,2-OCHF₂-3,6-F₂, 2-OCF₃, 2-OCF₃-4-F, 2-OCF₃-5-F, 2-OCF₃-6-F,2-OCF₃-4-CF₃, 2-OCF₃-5-CF₃, 2-OCF₃-6-CF₃, 2-OCF₃-3,6-F₂, 2-Cl-3-Br-6-F,2-Cl-5-CF₃, 2,5,6-C₁₃, 2-CF₃-5-Cl, 2,6-Cl₂, 2-Br-4-F, 2,4,6-C₁₃,2-Br-4-F-6-Cl, 2-Br-4,6-Cl₂, 2-Br-4,6-F₂, 2,4-Cl₂-6-F, 2-CF₃-4,6-Cl₂,2-CF₃-4-F-6-Cl, 2-CF₃-4,6-F₂, 2,6-Cl₂, 2-Br-4-F, 2,4,6-C₁₃,2-Br-4-F-6-Cl, 2-Br-4,6-Cl₂, 2-Br-4,6-F₂, 2,4-Cl₂-6-F, 2-CF₃-4,6-Cl₂,2-CF₃-4-F-6-Cl or 2-CF₃-4,6-F₂.

In further preferred aspects of the formula I.1, the groups R¹, R², R³,R⁴ and R⁵ together form the following substitution patterns: 2-Br, 2-Cl,2,4-Cl₂, 2-Cl-4-F, 2-Cl-5-F, 2-Cl-6-F, 2-Cl-4-CF₃, 2-Cl-5-CF₃,2-Cl-6-CF₃, 2-Cl-3,6-F₂, 2-F, 2,4-F₂, 2,5-F₂, 2,6-F₂, 2-F-4-CF₃,2-F-5-CF₃, 2-F-6-CF₃, 2,3,6-F₃, 2-NO₂, 2-NO₂-4-F, 2-NO₂-5-F, 2-NO₂-6-F,2-NO₂-4-CF₃, 2-NO₂-5-CF₃, 2-NO₂-6-CF₃, 2-NO₂-3,6-F₂, 2-CN, 2-CH₃,2-CH₃-4-F, 2-CH₃-5-F, 2-CH₃-6-F, 2-CH₃-4-CF₃, 2-CH₃-5-CF₃, 2-CH₃-6-CF₃,2-CH₃-3,6-F₂, 2-OCH₃, 2-OCH₃-4-F, 2-OCH₃-5-F, 2-OCH₃-6-F, 2-OCH₃-4-CF₃,2-OCH₃-5-CF₃, 2-OCH₃-6-CF₃, 2-OCH₃-3,6-F₂, 2-CHF₂, 2-CHF₂-4-F,2-CHF₂-5-F, 2-CHF₂-6-F, 2-CHF₂-4-CF₃, 2-CHF₂-5-CF₃, 2-CHF₂-6-CF₃,2-CHF₂-3,6-F₂, 2-CF₃, 2-CF₃-4-F, 2-CF₃-5-F, 2-CF₃-6-F, 2-CF₃-4-CF₃,2-CF₃-5-CF₃, 2-CF₃-6-CF₃, 2-CF₃-3,6-F₂, 2-OCHF₂, 2-OCHF₂-4-F,2-OCHF₂-5-F, 2-OCHF₂-6-F, 2-OCHF₂-4-CF₃, 2-OCHF₂-5-CF₃, 2-OCHF₂-6-CF₃,2-OCHF₂-3,6-F₂, 2-OCF₃, 2-OCF₃-4-F, 2-OCF₃-5-F, 2-OCF₃-6-F,2-OCF₃-4-CF₃, 2-OCF₃-5-CF₃, 2-OCF₃-6-CF₃, 2-OCF₃-3,6-F₂, 2-Cl-3-Br-6-F,2-Cl-5-CF₃, 2,5,6-Cl₃ or 2-CF₃-5-Cl.

In a further preferred embodiment of the compounds of the formula I, Ais N. These compounds correspond to formula I.2,

in which the variables have the meanings defined at the outset andpreferably those mentioned above. In one embodiment, R¹ and R³ are nothalogen. Especially preferably, in compounds of the formula I.2 thegroup

-   R¹ is nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₁-C₄-alkoxy-C₁-C₄-alkoxy C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio or    C₁-C₄-alkylsulfonyl, in particular NO₂, CH₃, CF₃, CH₂OCH₂CH₂OCH₃,    OCH₃, OCF₃, OCHF₂, SCF₃, SCHF₂, SO₂CH₃;-   R³ is H, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,    C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl, in particular H, CN, NO₂, CH₃,    CH₂CH₃, CF₃, CHF₂, OCH₃, OCF₃, OCHF₂, SCH₃, SO₂CH₃ or SO₂CH₂CH₃;-   R⁴, R⁵ are H.

In a further preferred embodiment of the compounds of the formula I, R⁴is hydrogen, halogen or C₁-C₄-haloalkyl, in particular H.

In a further preferred embodiment of the compounds of the formula I, R⁵is hydrogen or halogen, particularly preferably H, F or Cl, inparticular H.

In a further preferred embodiment of the compounds of the formula I, oneof the groups R⁴ and R⁵ is halogen, such as Cl or F.

In a further preferred embodiment of the compounds of the formula I, R⁶is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkoxy or C₁-C₄-haloalkylthio, particularlypreferably H, CH₃, CF₃, CHF₂, OCH₃, OCF₃, OCHF₂, SCH₃, SCF₃, SCHF₂, inparticular H.

In further preferred embodiments:

R⁷ is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H; and

R⁸ is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H.

In a further preferred embodiment of the compounds of the formula I, atleast one of the groups R⁷ and R⁸, preferably both groups, is/arehydrogen.

R^(x) is preferably H, C₁-C₆-alkyl, such as CH₃, C₂H₅, n-C₃H₇, CH(CH₃)₂,n-C₃H₉, or C(CH₃)₃; C₃-C₆-cycloalkyl-C₁-C₄-alkyl, such ascyclopropylmethyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, such as CH₂CH═CH₂,CH₂C(CH₃)═CH₂, CH₂CH₂H═CH₂, CH₂CH₂C(CH₃)—CH₂, CH₂CH₂CH₂CH═CH₂,CH₂CH₂CH₂C(CH₃)═CH₂, CH₂C≡CH, or optionally subst. phenyl, such as C₆H₅,4-CH₃—C₆H₄, 4-F—C₆H₄ or S(O)_(n)—R^(N), where RN is C₁-C₆-haloalkyl,such as CH₂CF₃, CH₂CHF₂. Particularly preferably, R^(x) is C₁-C₆-alkylor C₁-C₄-haloalkyl.

A further embodiment relates to the N-oxides of the compounds of theformula I.

A further embodiment relates to salts of the compounds of the formula I,in particular those which are obtainable by quaternization of apyridazine nitrogen atom, which may preferably take place by alkylationor arylation of the compounds of the formula I. Preferred salts of thecompounds are thus the N-alkyl salts, in particular the N-methyl salts,and the N-phenyl salts.

In particular with a view to their use, preference is given to thecompounds of the formula I compiled in the tables below, which compoundscorrespond to the formulae I.1A and I.2A. The groups mentioned for asubstituent in the tables are furthermore per se, independently of thecombination in which they are mentioned, a particularly preferred aspectof the substituent in question.

Table 1

Compounds of the formula I, in which R^(x) is CH₃, R is OH, R⁶ is H andthe combination of R¹ to R⁵ for a compound corresponds in each case toone row of table A or is specified in any of tables A.1 to A.8

Table 2

Compounds of the formula I, in which R^(x) is CH₃, R is OCH₂CH═CH₂, R⁶is H and the combination of R¹ to R⁵ for a compound corresponds in eachcase to one row of table A or is specified in any of tables A.1 to A.8

Table 3

Compounds of the formula I, in which R^(x) is CH₃, R is OCH₂C≡CH, R⁶ isH and the combination of R¹ to R⁵ for a compound corresponds in eachcase to one row of table A or is specified in any of tables A.1 to A.8

Table 4

Compounds of the formula I, in which R^(x) is CH₃, R is OH, R⁶ is CH₃and the combination of R¹ to R⁵ for a compound corresponds in each caseto one row of table A or is specified in any of tables A.1 to A.8

Table 5

Compounds of the formula I, in which R^(x) is CH₃, R is OCH₂CH═CH₂, R⁶is CH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 6

Compounds of the formula I, in which R^(x) is CH₃, R is OCH₂C≡CH, R⁶ isCH₃ and the combination of R¹ to R⁵ for a compound corresponds in eachcase to one row of table A or is specified in any of tables A.1 to A.8

Table 7

Compounds of the formula I, in which R^(x) is CH₃, R is OH, R⁶ is CH₂CH₃and the combination of R¹ to R⁵ for a compound corresponds in each caseto one row of table A or is specified in any of tables A.1 to A.8

Table 8

Compounds of the formula I, in which R^(x) is CH₃, R is OCH₂CH═CH₂, R⁶is CH₂CH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 9

Compounds of the formula I, in which R^(x) is CH₃, R is OCH₂C≡CH, R⁶ isCH₂CH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 10

Compounds of the formula I, in which R^(x) is CH₃, R is OH, R⁶ is OCH₃and the combination of R¹ to R⁵ for a compound corresponds in each caseto one row of table A or is specified in any of tables A.1 to A.8

Table 11

Compounds of the formula I, in which R^(x) is CH₃, R is OCH₂CH═CH₂, R⁶is OCH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 12

Compounds of the formula I, in which R^(x) is CH₃, R is OCH₂C≡CH, R⁶ isOCH₃ and the combination of R¹ to R⁵ for a compound corresponds in eachcase to one row of table A or is specified in any of tables A.1 to A.8

Table 13

Compounds of the formula I, in which R^(x) is CH₃, R is OH, R⁶ is SCH₃and the combination of R¹ to R⁵ for a compound corresponds in each caseto one row of table A or is specified in any of tables A.1 to A.8

Table 14

Compounds of the formula I, in which R^(x) is CH₃, R is OCH₂CH═CH₂, R⁶is SCH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 15

Compounds of the formula I, in which R^(x) is CH₃, R is OCH₂C≡CH, R⁶ isSCH₃ and the combination of R¹ to R⁵ for a compound corresponds in eachcase to one row of table A or is specified in any of tables A.1 to A.8

Table 16

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OH, R⁶ is Hand the combination of R¹ to R⁵ for a compound corresponds in each caseto one row of table A or is specified in any of tables A.1 to A.8

Table 17

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OCH₂CH═CH₂,R⁶ is H and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 18

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OCH₂C≡CH, R⁶is H and the combination of R¹ to R⁵ for a compound corresponds in eachcase to one row of table A or is specified in any of tables A.1 to A.8

Table 19

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OH, R⁶ is CH₃and the combination of R¹ to R⁵ for a compound corresponds in each caseto one row of table A or is specified in any of tables A.1 to A.8

Table 20

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OCH₂CH═CH₂,R⁶ is CH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 21

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OCH₂C≡CH, R⁶is CH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 22

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OH, R⁶ isCH₂CH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 23

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OCH₂CH═CH₂,R⁶ is CH₂CH₃ and the combination of R¹ to R⁵ for a compound correspondsin each case to one row of table A or is specified in any of tables A.1to A.8

Table 24

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OCH₂C≡CH, R⁶is CH₂CH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 25

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OH, R⁶ isOCH₃ and the combination of R¹ to R⁵ for a compound corresponds in eachcase to one row of table A or is specified in any of tables A.1 to A.8

Table 26

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OCH₂CH═CH₂,R⁶ is OCH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 27

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OCH₂C≡CH, R⁶is OCH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 28

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OH, R⁶ isSCH₃ and the combination of R¹ to R⁵ for a compound corresponds in eachcase to one row of table A or is specified in any of tables A.1 to A.8

Table 29

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OCH₂CH═CH₂,R⁶ is SCH₃ and the combination of R¹, R³ and if appropriate R² for acompound corresponds in each case to one row of table A or is specifiedin any of tables A.1 to A.8

Table 30

Compounds of the formula I, in which R^(x) is CH₂CH₃, R is OCH₂C≡CH, R⁶is SCH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 31

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OH, R⁶ is Hand the combination of R¹ to R⁵ for a compound corresponds in each caseto one row of table A or is specified in any of tables A.1 to A.8

Table 32

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OCH₂CH═CH₂,R⁶ is H and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 33

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OCH₂C≡CH, R⁶is H and the combination of R¹ to R⁵ for a compound corresponds in eachcase to one row of table A or is specified in any of tables A.1 to A.8

Table 34

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OH, R⁶ isCH₃ and the combination of R¹ to R⁵ for a compound corresponds in eachcase to one row of table A or is specified in any of tables A.1 to A.8

Table 35

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OCH₂CH═CH₂,R⁶ is CH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 36

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OCH₂C≡CH, R⁶is CH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 37

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OH, R⁶ isCH₂CH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 38

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OCH₂CH═CH₂,R⁶ is CH₂CH₃ and the combination of R¹ to R⁵ for a compound correspondsin each case to one row of table A or is specified in any of tables A.1to A.8

Table 39

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OCH₂C≡CH, R⁶is CH₂CH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 40

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OH, R⁶ isOCH₃ and the combination of R¹ to R⁵ for a compound corresponds in eachcase to one row of table A or is specified in any of tables A.1 to A.8

Table 41

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OCH₂CH═CH₂,R⁶ is OCH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 42

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OCH₂C≡CH, R⁶is OCH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 43

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OH, R⁶ isSCH₃ and the combination of R¹ to R⁵ for a compound corresponds in eachcase to one row of table A or is specified in any of tables A.1 to A.8

Table 44

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OCH₂CH═CH₂,R⁶ is SCH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

Table 45

Compounds of the formula I, in which R^(x) is CH₂CHF₂, R is OCH₂C≡CH, R⁶is SCH₃ and the combination of R¹ to R⁵ for a compound corresponds ineach case to one row of table A or is specified in any of tables A.1 toA.8

TABLE A Compounds of the formula I which correspond to the formulae I.1Aand I.2A I.1A

I.2A

No. Formula R¹ R² R³ R⁴ R⁵ A-1 I.1A Cl H H H H A-2 I.1A Br H H H H A-3I.1A CH₃ H H H H A-4 I.1A CF₃ H H H H A-5 I.1A OCF₃ H H H H A-6 I.1ASCF₃ H H H H A-7 I.1A Cl Cl H H H A-8 I.1A Br Cl H H H A-9 I.1A CH₃ Cl HH H A-10 I.1A CF₃ Cl H H H A-11 I.1A OCF₃ Cl H H H A-12 I.1A SCF₃ Cl H HH A-13 I.1A Cl F H H H A-14 I.1A Br F H H H A-15 I.1A CH₃ F H H H A-16I.1A CF₃ F H H H A-17 I.1A OCF₃ F H H H A-18 I.1A SCF₃ F H H H A-19 I.1ACl H Cl H H A-20 I.1A Br H Cl H H A-21 I.1A CH₃ H Cl H H A-22 I.1A CF₃ HCl H H A-23 I.1A OCF₃ H Cl H H A-24 I.1A SCF₃ H Cl H H A-25 I.1A Cl H FH H A-26 I.1A Br H F H H A-27 I.1A CH₃ H F H H A-28 I.1A CF₃ H F H HA-29 I.1A OCF₃ H F H H A-30 I.1A SCF₃ H F H H A-31 I.1A Cl H CF₃ H HA-32 I.1A Br H CF₃ H H A-33 I.1A CH₃ H CF₃ H H A-34 I.1A CF₃ H CF₃ H HA-35 I.1A OCF₃ H CF₃ H H A-36 I.1A SCF₃ H CF₃ H H A-37 I.1A Cl H H Cl HA-38 I.1A Br H H Cl H A-39 I.1A CH₃ H H Cl H A-40 I.1A CF₃ H H Cl H A-41I.1A OCF₃ H H Cl H A-42 I.1A SCF₃ H H Cl H A-43 I.1A Cl H H F H A-44I.1A Br H H F H A-45 I.1A CH₃ H H F H A-46 I.1A CF₃ H H F H A-47 I.1AOCF₃ H H F H A-48 I.1A SCF₃ H H F H A-49 I.1A Cl H H CF₃ H A-50 I.1A BrH H CF₃ H A-51 I.1A CH₃ H H CF₃ H A-52 I.1A CF₃ H H CF₃ H A-53 I.1A OCF₃H H CF₃ H A-54 I.1A SCF₃ H H CF₃ H A-55 I.1A Cl H H H Cl A-56 I.1A Br HH H Cl A-57 I.1A CH₃ H H H Cl A-58 I.1A CF₃ H H H Cl A-59 I.1A OCF₃ H HH Cl A-60 I.1A SCF₃ H H H Cl A-61 I.1A Cl H H H F A-62 I.1A Br H H H FA-63 I.1A CH₃ H H H F A-64 I.1A CF₃ H H H F A-65 I.1A OCF₃ H H H F A-66I.1A SCF₃ H H H F A-67 I.1A Cl F H H F A-68 I.1A Br F H H F A-69 I.1ACH₃ F H H F A-70 I.1A CF₃ F H H F A-71 I.1A OCF₃ F H H F A-72 I.1A SCF₃F H H F A-73 I.1A Cl

H H H A-74 I.1A Cl

CH₃ H H A-75 I.1A Cl

CF₃ H H A-76 I.1A Cl

CHF₂ H H A-77 I.1A Cl

OCH₃ H H A-78 I.1A Cl

OCHF₂ H H A-79 I.1A Cl

SCH₃ H H A-80 I.1A Cl

H H H A-81 I.1A Cl

CH₃ H H A-82 I.1A Cl

CF₃ H H A-83 I.1A Cl

CHF₂ H H A-84 I.1A Cl

OCH₃ H H A-85 I.1A Cl

OCHF₂ H H A-86 I.1A Cl

SCH₃ H H A-87 I.1A Cl

H H H A-88 I.1A Cl

CH₃ H H A-89 I.1A Cl

CF₃ H H A-90 I.1A Cl

CHF₂ H H A-91 I.1A Cl

OCH₃ H H A-92 I.1A Cl

OCHF₂ H H A-93 I.1A Cl

SCH₃ H H A-94 I.1A Cl

H H H A-95 I.1A Cl

CH₃ H H A-96 I.1A Cl

CF₃ H H A-97 I.1A Cl

CHF₂ H H A-98 I.1A Cl

OCH₃ H H A-99 I.1A Cl

OOCHF₂ H H A-100 I.1A Cl

SCH₃ H H A-101 I.1A Cl

H H H A-102 I.1A Cl

CH₃ H H A-103 I.1A Cl

CF₃ H H A-104 I.1A Cl

CHF₂ H H A-105 I.1A Cl

OCH₃ H H A-106 I.1A Cl

OCHF₂ H H A-107 I.1A Cl

SCH₃ H H A-108 I.1A Cl

H H H A-109 I.1A Cl

CH₃ H H A-110 I.1A Cl

CF₃ H H A-111 I.1A Cl

CHF₂ H H A-112 I.1A Cl

OCH₃ H H A-113 I.1A Cl

OCHF₂ H H A-114 I.1A Cl

SCH₃ H H A-115 I.1A Cl

H H H A-116 I.1A Cl

CH₃ H H A-117 I.1A Cl

CF₃ H H A-118 I.1A Cl

CHF₂ H H A-119 I.1A Cl

OCH₃ H H A-120 I.1A Cl

OCHF₂ H H A-121 I.1A Cl

SCH₃ H H A-122 I.1A Cl

H H H A-123 I.1A Cl

CH₃ H H A-124 I.1A Cl

CF₃ H H A-125 I.1A Cl

CHF₂ H H A-126 I.1A Cl

OCH₃ H H A-127 I.1A Cl

OCHF₂ H H A-128 I.1A Cl

SCH₃ H H A-129 I.1A Cl

H H H A-130 I.1A Cl

CH₃ H H A-131 I.1A Cl

CF₃ H H A-132 I.1A Cl

CHF₂ H H A-133 I.1A Cl

OCH₃ H H A-134 I.1A Cl

OCHF₂ H H A-135 I.1A Cl

SCH₃ H H A-136 I.1A Cl

H H H A-137 I.1A Cl

CH₃ H H A-138 I.1A Cl

CF₃ H H A-139 I.1A Cl

CHF₂ H H A-140 I.1A Cl

OCH₃ H H A-141 I.1A Cl

OCHF₂ H H A-142 I.1A Cl

SCH₃ H H A-143 I.1A Cl C₆H₅ H H H A-144 I.1A Cl C₆H₅ CH₃ H H A-145 I.1ACl C₆H₅ CF₃ H H A-146 I.1A Cl C₆H₅ CHF₂ H H A-147 I.1A Cl C₆H₅ OCH₃ H HA-148 I.1A Cl C₆H₅ OCHF₂ H H A-149 I.1A Cl C₆H₅ SCH₃ H H A-150 I.1A Cl4-OCH₃—C₆H₄ H H H A-151 I.1A Cl 4-OCH₃—C₆H₄ CH₃ H H A-152 I.1A Cl4-OCH₃—C₆H₄ CF₃ H H A-153 I.1A Cl 4-OCH₃—C₆H₄ CHF₂ H H A-154 I.1A Cl4-OCH₃—C₆H₄ OCH₃ H H A-155 I.1A Cl 4-OCH₃—C₆H₄ OCHF₂ H H A-156 I.1A Cl4-OCH₃—C₆H₄ SCH₃ H H A-157 I.1A Cl CH═CH₂ H H H A-158 I.1A Cl CH═CH₂ CH₃H H A-159 I.1A Cl CH═CH₂ CF₃ H H A-160 I.1A Cl CH═CH₂ CHF₂ H H A-161I.1A Cl CH═CH₂ OCH₃ H H A-162 I.1A Cl CH═CH₂ OCHF₂ H H A-163 I.1A ClCH═CH₂ SCH₃ H H A-164 I.1A Cl CH═CH—CH₃ H H H A-165 I.1A Cl CH═CH—CH₃CH₃ H H A-166 I.1A Cl CH═CH—CH₃ CF₃ H H A-167 I.1A Cl CH═CH—CH₃ CHF₂ H HA-168 I.1A Cl CH═CH—CH₃ OCH₃ H H A-169 I.1A Cl CH═CH—CH₃ OCHF₂ H H A-170I.1A Cl CH═CH—CH₃ SCH₃ H H A-171 I.1A Cl CH₂CH═CH₂ H H H A-172 I.1A ClCH₂CH═CH₂ CH₃ H H A-173 I.1A Cl CH₂CH═CH₂ CF₃ H H A-174 I.1A ClCH₂CH═CH₂ CHF₂ H H A-175 I.1A Cl CH₂CH═CH₂ OCH₃ H H A-176 I.1A ClCH₂CH═CH₂ OCHF₂ H H A-177 I.1A Cl CH₂CH═CH₂ SCH₃ H H A-178 I.1A Cl CH₂C≡CH H H H A-179 I.1A Cl CH₂C≡ CH CH₃ H H A-180 I.1A Cl CH₂C≡ CH CF₃ H HA-181 I.1A Cl CH₂C≡ CH CHF₂ H H A-182 I.1A Cl CH₂C≡ CH OCH₃ H H A-183I.1A Cl CH₂C≡ CH OCHF₂ H H A-184 I.1A Cl CH₂C≡ CH SCH₃ H H A-185 I.1A ClCH₂OCH₂CF₃ H H H A-186 I.1A Cl CH₂OCH₂CF₃ CH₃ H H A-187 I.1A ClCH₂OCH₂CF₃ CF₃ H H A-188 I.1A Cl CH₂OCH₂CF₃ CHF₂ H H A-189 I.1A ClCH₂OCH₂CF₃ OCH₃ H H A-190 I.1A Cl CH₂OCH₂CF₃ OCHF₂ H H A-191 I.1A ClCH₂OCH₂CF₃ SCH₃ H H A-192 I.1A Cl

H H H A-193 I.1A Cl

CH₃ H H A-194 I.1A Cl

CF₃ H H A-195 I.1A Cl

CHF₂ H H A-196 I.1A Cl

OCH₃ H H A-197 I.1A Cl

OCHF₂ H H A-198 I.1A Cl

SCH₃ H H A-199 I.1A Cl OCH₂CH₃ H H H A-200 I.1A Cl OCH₂CH₃ CH₃ H H A-201I.1A Cl OCH₂CH₃ CF₃ H H A-202 I.1A Cl OCH₂CH₃ CHF₂ H H A-203 I.1A ClOCH₂CH₃ OCH₃ H H A-204 I.1A Cl OCH₂CH₃ OCHF₂ H H A-205 I.1A Cl OCH₂CH₃SCH₃ H H A-206 I.1A Cl OCH₂CH₂OCH₃ H H H A-207 I.1A Cl OCH₂CH₂OCH₃ CH₃ HH A-208 I.1A Cl OCH₂CH₂OCH₃ CF₃ H H A-209 I.1A Cl OCH₂CH₂OCH₃ CHF₂ H HA-210 I.1A Cl OCH₂CH₂OCH₃ OCH₃ H H A-211 I.1A Cl OCH₂CH₂OCH₃ OCHF₂ H HA-212 I.1A Cl OCH₂CH₂OCH₃ SCH₃ H H A-213 I.1A Cl SO₂CH₃ H H H A-214 I.1ACl SO₂CH₃ CH₃ H H A-215 I.1A Cl SO₂CH₃ CF₃ H H A-216 I.1A Cl SO₂CH₃ CHF₂H H A-217 I.1A Cl SO₂CH₃ OCH₃ H H A-218 I.1A Cl SO₂CH₃ OCHF₂ H H A-219I.1A Cl SO₂CH₃ SCH₃ H H A-220 I.1A Cl SO₂CH₂CH₃ H H H A-221 I.1A ClSO₂CH₂CH₃ CH₃ H H A-222 I.1A Cl SO₂CH₂CH₃ CF₃ H H A-223 I.1A ClSO₂CH₂CH₃ CHF₂ H H A-224 I.1A Cl SO₂CH₂CH₃ OCH₃ H H A-225 I.1A ClSO₂CH₂CH₃ OCHF₂ H H A-226 I.1A Cl SO₂CH₂CH₃ SCH₃ H H A-227 I.1A ClSO₂CH(CH₃)₂ H H H A-228 I.1A Cl SO₂CH(CH₃)₂ CH H H A-229 I.1A ClSO₂CH(CH₃)₂ CF₃ H H A-230 I.1A Cl SO₂CH(CH₃)₂ CHF₂ H H A-231 I.1A ClSO₂CH(CH₃)₂ OCH₃ H H A-232 I.1A Cl SO₂CH(CH₃)₂ OCHF₂ H H A-233 I.1A ClSO₂CH(CH₃)₂ SCH₃ H H A-234 I.1A Cl COOCH₃ H H H A-235 I.1A Cl COOCH₃ CH₃H H A-236 I.1A Cl COOCH₃ CF₃ H H A-237 I.1A Cl COOCH₃ CHF₂ H H A-238I.1A Cl COOCH₃ OCH₃ H H A-239 I.1A Cl COOCH₃ OCHF₂ H H A-240 I.1A ClCOOCH₃ SCH₃ H H A-241 I.1A Cl COOCH₂CH₃ H H H A-242 I.1A Cl COOCH₂CH₃CH₃ H H A-243 I.1A Cl COOCH₂CH₃ CF₃ H H A-244 I.1A Cl COOCH₂CH₃ CHF₂ H HA-245 I.1A Cl COOCH₂CH₃ OCH₃ H H A-246 I.1A Cl COOCH₂CH₃ OCHF₂ H H A-247I.1A Cl COOCH₂CH₃ SCH₃ H H A-248 I.1A Cl #²-CH₂CH₂SO₂-#³ H H A-249 I.1ACl #²-CH(CH₃)CH₂SO₂-#³ H H A-250 I.1A Cl #²-C(CH₃)₂CH₂SO₂-#³ H H A-251I.1A Cl #²-SO₂CH₂CH₂SO₂-#³ H H A-252 I.1A Cl #²-CH(OCH₂CH₂F)CH₂CH₂SO₂-#³H H A-253 I.1A Cl #²-C(C═NOCH₃)CH₂CH₂SO₂-#³ H H A-254 I.1A Cl#²-SO₂CH₂CH₂C(CH₃)₂-#³ H H A-255 I.1A Cl #²-N(CH₃)C(═)S-#³ H H A-256I.1A Cl #²-C(═O)N(CH₃)SO₂-#³ H H A-257 I.1A Br

H H H A-258 I.1A Br

CH₃ H H A-259 I.1A Br

CF₃ H H A-260 I.1A Br

CHF₂ H H A-261 I.1A Br

OCH₃ H H A-262 I.1A Br

OCHF₂ H H A-263 I.1A Br

SCH₃ H H A-264 I.1A Br

H H H A-265 I.1A Br

CH₃ H H A-266 I.1A Br

CF₃ H H A-267 I.1A Br

CHF₂ H H A-268 I.1A Br

OCH₃ H H A-269 I.1A Br

OCHF₂ H H A-270 I.1A Br

SCH₃ H H A-271 I.1A Br

H H H A-272 I.1A Br

CH₃ H H A-273 I.1A Br

CF₃ H H A-274 I.1A Br

CHF₂ H H A-275 I.1A Br

OCH₃ H H A-276 I.1A Br

OCHF₂ H H A-277 I.1A Br

SCH₃ H H A-278 I.1A Br

H H H A-279 I.1A Br

CH₃ H H A-280 I.1A Br

CF₃ H H A-281 I.1A Br

CHF₂ H H A-282 I.1A Br

OCH₃ H H A-283 I.1A Br

OCHF₂ H H A-284 I.1A Br

SCH₃ H H A-285 I.1A Br

H H H A-286 I.1A Br

CH₃ H H A-287 I.1A Br

CF₃ H H A-288 I.1A Br

CHF₂ H H A-289 I.1A Br

OCH₃ H H A-290 I.1A Br

OCHF₂ H H A-291 I.1A Br

SCH₃ H H A-292 I.1A Br

H H H A-293 I.1A Br

CH₃ H H A-294 I.1A Br

CF₃ H H A-295 I.1A Br

CHF₂ H H A-296 I.1A Br

OCH₃ H H A-297 I.1A Br

OCHF₂ H H A-298 I.1A Br

SCH₃ H H A-299 I.1A Br

H H H A-300 I.1A Br

CH₃ H H A-301 I.1A Br

CF₃ H H A-302 I.1A Br

CHF₂ H H A-303 I.1A Br

OCH₃ H H A-304 I.1A Br

OCHF₂ H H A-305 I.1A Br

SCH₃ H H A-306 I.1A Br

H H H A-307 I.1A Br

CH₃ H H A-308 I.1A Br

CF₃ H H A-309 I.1A Br

CHF₂ H H A-310 I.1A Br

OCH₃ H H A-311 I.1A Br

OCHF₂ H H A-312 I.1A Br

SCH₃ H H A-313 I.1A Br

H H H A-314 I.1A Br

CH₃ H H A-315 I.1A Br

CF₃ H H A-316 I.1A Br

CHF₂ H H A-317 I.1A Br

OCH₃ H H A-318 I.1A Br

OCHF₂ H H A-319 I.1A Br

SCH₃ H H A-320 I.1A Br

H H H A-321 I.1A Br

CH₃ H H A-322 I.1A Br

CF₃ H H A-323 I.1A Br

CHF₂ H H A-324 I.1A Br

OCH₃ H H A-325 I.1A Br

OCHF₂ H H A-326 I.1A Br

SCH₃ H H A-327 I.1A Br C₆H₅ H H H A-328 I.1A Br C₆H₅ CH₃ H H A-329 I.1ABr C₆H₅ CF₃ H H A-330 I.1A Br C₆H₅ CHF₂ H H A-331 I.1A Br C₆H₅ OCH₃ H HA-332 I.1A Br C₆H₅ OCHF₂ H H A-333 I.1A Br C₆H₅ SCH₃ H H A-334 I.1A Br4-OCH₃—C₆H₄ H H H A-335 I.1A Br 4-OCH₃—C₆H₄ CH₃ H H A-336 I.1A Br4-OCH₃—C₆H₄ CF₃ H H A-337 I.1A Br 4-OCH₃—C₆H₄ CHF₂ H H A-338 I.1A Br4-OCH₃—C₆H₄ OCH₃ H H A-339 I.1A Br 4-OCH₃—C₆H₄ OCHF₂ H H A-340 I.1A Br4-OCH₃—C₆H₄ SCH₃ H H A-341 I.1A Br CH═CH₂ H H H A-342 I.1A Br CH═CH₂ CH₃H H A-343 I.1A Br CH═CH₂ CF₃ H H A-344 I.1A Br CH═CH₂ CHF₂ H H A-345I.1A Br CH═CH₂ OCH₃ H H A-346 I.1A Br CH═CH₂ OCHF₂ H H A-347 I.1A BrCH═CH₂ SCH₃ H H A-348 I.1A Br CH═CH—CH₃ H H H A-349 I.1A Br CH═CH—CH₃CH₃ H H A-350 I.1A Br CH═CH—CH₃ CF₃ H H A-351 I.1A Br CH═CH—CH₃ CHF₂ H HA-352 I.1A Br CH═CH—CH₃ OCH₃ H H A-353 I.1A Br CH═CH—CH₃ OCHF₂ H H A-354I.1A Br CH═CH—CH₃ SCH₃ H H A-355 I.1A Br CH₂CH═CH₂ H H H A-356 I.1A BrCH₂CH═CH₂ CH₃ H H A-357 I.1A Br CH₂CH═CH₂ CF₃ H H A-358 I.1A BrCH₂CH═CH₂ CHF₂ H H A-359 I.1A Br CH₂CH═CH₂ OCH₃ H H A-360 I.1A BrCH₂CH═CH₂ OCHF₂ H H A-361 I.1A Br CH₂CH═CH₂ SCH₃ H H A-362 I.1A Br CH₂C≡CH H H H A-363 I.1A Br CH₂C≡ CH CH₃ H H A-364 I.1A Br CH₂C≡ CH CF₃ H HA-365 I.1A Br CH₂C≡ CH CHF₂ H H A-366 I.1A Br CH₂C≡ CH OCH₃ H H A-367I.1A Br CH₂C≡ CH OCHF₂ H H A-368 I.1A Br CH₂C≡ CH SCH₃ H H A-369 I.1A BrCH₂OCH₂CF₃ H H H A-370 I.1A Br CH₂OCH₂CF₃ CH₃ H H A-371 I.1A BrCH₂OCH₂CF₃ CF₃ H H A-372 I.1A Br CH₂OCH₂CF₃ CHF₂ H H A-373 I.1A BrCH₂OCH₂CF₃ OCH₃ H H A-374 I.1A Br CH₂OCH₂CF₃ OCHF₂ H H A-375 I.1A BrCH₂OCH₂CF₃ SCH₃ H H A-376 I.1A Br

H H H A-377 I.1A Br

CH₃ H H A-378 I.1A Br

CF₃ H H A-379 I.1A Br

CHF₂ H H A-380 I.1A Br

OCH₃ H H A-381 I.1A Br

OCHF₂ H H A-382 I.1A Br

SCH₃ H H A-383 I.1A Br OCH₂CH₃ H H H A-384 I.1A Br OCH₂CH₃ CH₃ H H A-385I.1A Br OCH₂CH₃ CF₃ H H A-386 I.1A Br OCH₂CH₃ CHF₂ H H A-387 I.1A BrOCH₂CH₃ OCHF₂ H H A-388 I.1A Br OCH₂CH₃ OCHF₂ H H A-389 I.1A Br OCH₂CH₃SCH₃ H H A-390 I.1A Br OCH₂CH₂OCH₃ H H H A-391 I.1A Br OCH₂CH₂OCH₃ CH₃ HH A-392 I.1A Br OCH₂CH₂OCH₃ CF₃ H H A-393 I.1A Br OCH₂CH₂OCH₃ CHF₂ H HA-394 I.1A Br OCH₂CH₂OCH₃ OCH₃ H H A-395 I.1A Br OCH₂CH₂OCH₃ OCHF₂ H HA-396 I.1A Br OCH₂CH₂OCH₃ SCH₃ H H A-397 I.1A Br SO₂CH₃ H H H A-398 I.1ABr SO₂CH₃ CH₃ H H A-399 I.1A Br SO₂CH₃ CF₃ H H A-400 I.1A Br SO₂CH₃ CHF₂H H A-401 I.1A Br SO₂CH₃ OCH₃ H H A-402 I.1A Br SO₂CH₃ OCHF₂ H H A-403I.1A Br SO₂CH₃ SCH₃ H H A-404 I.1A Br SO₂CH₂CH₃ H H H A-405 I.1A BrSO₂CH₂CH₃ CH₃ H H A-406 I.1A Br SO₂CH₂CH₃ CF₃ H H A-407 I.1A BrSO₂CH₂CH₃ CHF₂ H H A-408 I.1A Br SO₂CH₂CH₃ OCH₃ H H A-409 I.1A BrSO₂CH₂CH₃ OCHF₂ H H A-410 I.1A Br SO₂CH₂CH₃ SCH₃ H H A-411 I.1A BrSO₂CH(CH₃)₂ H H H A-412 I.1A Br SO₂CH(CH₃)₂ CH₃ H H A-413 I.1A BrSO₂CH(CH₃)₂ CF₃ H H A-414 I.1A Br SO₂CH(CH₃)₂ CHF₂ H H A-415 I.1A BrSO₂CH(CH₃)₂ OCH₃ H H A-416 I.1A Br SO₂CH(CH₃)₂ OCHF₂ H H A-417 I.1A BrSO₂CH(CH₃)₂ SCH₃ H H A-418 I.1A Br COOCH₃ H H H A-419 I.1A Br COOCH₃ CH₃H H A-420 I.1A Br COOCH₃ CF₃ H H A-421 I.1A Br COOCH₃ CHF₂ H H A-422I.1A Br COOCH₃ OCH₃ H H A-423 I.1A Br COOCH₃ OCHF₂ H H A-424 I.1A BrCOOCH₃ SCH₃ H H A-425 I.1A Br COOCH₂CH₃ H H H A-426 I.1A Br COOCH₂CH₃CH₃ H H A-427 I.1A Br COOCH₂CH₃ CF₃ H H A-428 I.1A Br COOCH₂CH₃ CHF₂ H HA-429 I.1A Br COOCH₂CH₃ OCH₃ H H A-430 I.1A Br COOCH₂CH₃ OCHF₂ H H A-431I.1A Br COOCH₂CH₃ SCH₃ H H A-432 I.1A Br #²-CH₂CH₂SO₂-#³ H H A-433 I.1ABr #²-CH(CH₃)CH₂SO₂-#³ H H A-434 I.1A Br #²-C(CH₃)₂CH₂SO₂-#³ H H A-435I.1A Br #²-SO₂CH₂CH₂SO₂-#³ H H A-436 I.1A Br #²-CH(OCH₂CH₂F)CH₂CH₂SO₂-#³H H A-437 I.1A Br #²-C(═NOCH₃)CH₂CH₂SO₂-#³ H H A-438 I.1A Br#²-SO₂CH₂CH₂C(CH₃)₂-#³ H H A-439 I.1A Br #²-N(CH₃)C(═O)S-#³ H H A-440I.1A Br #²-C(═O)N(CH₃)SO₂-#³ H H A-441 I.1A CH₃

H H H A-442 I.1A CH₃

CH₃ H H A-443 I.1A CH₃

CF₃ H H A-444 I.1A CH₃

CHF₂ H H A-445 I.1A CH₃

OCH₃ H H A-446 I.1A CH₃

OCHF₂ H H A-447 I.1A CH₃

SCH₃ H H A-448 I.1A CH₃

H H H A-449 I.1A CH₃

CH₃ H H A-450 I.1A CH₃

CF₃ H H A-451 I.1A CH₃

CHF₂ H H A-452 I.1A CH₃

OCH₃ H H A-453 I.1A CH₃

OCHF₂ H H A-454 I.1A CH₃

SCH₃ H H A-455 I.1A CH₃

H H H A-456 I.1A CH₃

CH₃ H H A-457 I.1A CH₃

CF₃ H H A-458 I.1A CH₃

CHF₂ H H A-459 I.1A CH₃

OCH₃ H H A-460 I.1A CH₃

OCHF₂ H H A-461 I.1A CH₃

SCH₃ H H A-462 I.1A CH₃

H H H A-463 I.1A CH₃

CH₃ H H A-464 I.1A CH₃

CF₃ H H A-465 I.1A CH₃

CHF₃ H H A-466 I.1A CH₃

OCH₃ H H A-467 I.1A CH₃

OCHF₂ H H A-468 I.1A CH₃

SCH₃ H H A-469 I.1A CH₃

H H H A-470 I.1A CH₃

CH₃ H H A-471 I.1A CH₃

CF₃ H H A-472 I.1A CH₃

CHF₂ H H A-473 I.1A CH₃

OCH₃ H H A-474 I.1A CH₃

OCHF₂ H H A-475 I.1A CH₃

SCH₃ H H A-476 I.1A CH₃

H H H A-477 I.1A CH₃

CH₃ H H A-478 I.1A CH₃

CF₃ H H A-479 I.1A CH₃

CHF₂ H H A-480 I.1A CH₃

OCH₃ H H A-481 I.1A CH₃

OCHF₂ H H A-482 I.1A CH₃

SCH₃ H H A-483 I.1A CH₃

H H H A-484 I.1A CH₃

CH₃ H H A-485 I.1A CH₃

CF₃ H H A-486 I.1A CH₃

CHF₂ H H A-487 I.1A CH₃

OCH₃ H H A-488 I.1A CH₃

OCHF₂ H H A-489 I.1A CH₃

SCH₃ H H A-490 I.1A CH₃

H H H A-491 I.1A CH₃

CH₃ H H A-492 I.1A CH₃

CF₃ H H A-493 I.1A CH₃

CHF₂ H H A-494 I.1A CH₃

OCH₃ H H A-495 I.1A CH₃

OCHF₂ H H A-496 I.1A CH₃

SCH₃ H H A-497 I.1A CH₃

H H H A-498 I.1A CH₃

CH₃ H H A-499 I.1A CH_(3/)

CF₃ H H A-500 I.1A CH₃

CHF₂ H H A-501 I.1A CH₃

OCH₃ H H A-502 I.1A CH₃

OCHF₂ H H A-503 I.1A CH₃

SCH₃ H H A-504 I.1A CH₃

H H H A-505 I.1A CH₃

CH₃ H H A-506 I.1A CH₃

CF₃ H H A-507 I.1A CH₃

CHF₂ H H A-508 I.1A CH₃

OCH₃ H H A-509 I.1A CH₃

OCHF₂ H H A-510 I.1A CH₃

SCH₃ H H A-511 I.1A CH₃ C₆H₅ H H H A-512 I.1A CH₃ C₆H₅ CH₃ H H A-513I.1A CH₃ C₆H₅ CF₃ H H A-514 I.1A CH₃ C₆H₅ CHF₂ H H A-515 I.1A CH₃ C₆H₅OCH₃ H H A-516 I.1A CH₃ C₆H5 OCHF₂ H H A-517 I.1A CH₃ C₆H₅ SCH₃ H HA-518 I.1A CH₃ 4-OCH₃—C₆H₄ H H H A-519 I.1A CH₃ 4-OCH₃—C₆H₄ CH₃ H HA-520 I.1A CH₃ 4-OCH₃—C₆H₄ CF₃ H H A-521 I.1A CH₃ 4-OCH₃—C₆H4 CHF₂ H HA-522 I.1A CH₃ 4-OCH₃—C₆H₄ OCH₃ H H A-523 I.1A CH₃ 4-OCH₃—C₆H4 OCHF₂ H HA-524 I.1A CH₃ 4-OCH₃—C₆H₄ SCH₃ H H A-525 I.1A CH₃ CH═CH₂ H H H A-526I.1A CH₃ CH═CH₂ CH₃ H H A-527 I.1A CH₃ CH═CH₂ CF₃ H H A-528 I.1A CH₃CH═CH₂ CHF₂ H H A-529 I.1A CH₃ CH═CH₂ OCH₃ H H A-530 I.1A CH₃ CH═CH₂OCHF₂ H H A-531 I.1A CH₃ CH═CH₂ SCH₃ H H A-532 I.1A CH₃ CH═CH—CH₃ H H HA-533 I.1A CH₃ CH═CH—CH₃ CH₃ H H A-534 I.1A CH₃ CH═CH—CH₃ CF₃ H H A-535I.1A CH₃ CH═CH—CH₃ CHF₂ H H A-536 I.1A CH₃ CH═CH—CH₃ OCH₃ H H A-537 I.1ACH₃ CH═CH—CH₃ OCHF₂ H H A-538 I.1A CH₃ CH═CH—CH₃ SCH₃ H H A-539 I.1A CH₃CH₂CH═CH₂ H H H A-540 I.1A CH₃ CH₂CH═CH₂ CH₃ H H A-541 I.1A CH₃CH₂CH═CH₂ CF₃ H H A-542 I.1A CH₃ CH₂CH═CH₂ CHF₂ H H A-543 I.1A CH₃CH₂CH═CH₂ OCH₃ H H A-544 I.1A CH₃ CH₂CH═CH₂ OCHF₂ H H A-545 I.1A CH₃CH₂CH═CH₂ SCH₃ H H A-546 I.1A CH₃ CH₂C≡ CH H H H A-547 I.1A CH₃ CH₂C≡ CHCH₃ H H A-548 I.1A CH₃ CH₂C≡ CH CF₃ H H A-549 I.1A CH₃ CH₂C≡ CH CHF₂ H HA-550 I.1A CH₃ CH₂C≡ CH OCH₃ H H A-551 I.1A CH₃ CH₂C≡ CH OCHF₂ H H A-552I.1A CH₃ CH₂C≡ CH SCH₃ H H A-553 I.1A CH₃ CH₂OCH₂CF₃ H H H A-554 I.1ACH₃ CH₂OCH₂CF₃ CH₃ H H A-555 I.1A CH₃ CH₂OCH₂CF₃ CF₃ H H A-556 I.1A CH₃CH₂OCH₂CF₃ CHF₂ H H A-557 I.1A CH₃ CH₂OCH₂CF₃ OCH₃ H H A-558 I.1A CH₃CH₂OCH₂CF₃ OCHF₂ H H A-559 I.1A CH₃ CH₂OCH₂CF₃ SCH₃ H H A-560 I.1A CH₃

H H H A-561 I.1A CH₃

CH₃ H H A-562 I.1A CH₃

CF₃ H H A-563 I.1A CH₃

CHF₂ H H A-564 I.1A CH₃

OCH₃ H H A-565 I.1A CH₃

OCHF₂ H H A-566 I.1A CH₃

SCH₃ H H A-567 I.1A CH₃ OCH₂CH₃ H H H A-568 I.1A CH₃ OCH₂CH₃ CH₃ H HA-569 I.1A CH₃ OCH₂CH₃ CF₃ H H A-570 I.1A CH₃ OCH₂CH₃ CHF₂ H H A-571I.1A CH₃ OCH₂CH₃ OCH₃ H H A-572 I.1A CH₃ OCH₂CH₃ OCHF₂ H H A-573 I.1ACH₃ OCH₂CH₃ SCH₃ H H A-574 I.1A CH₃ OCH₂CH₂OCH₃ H H H A-575 I.1A CH₃OCH₂CH₂OCH₃ CH₃ H H A-576 I.1A CH₃ OCH₂CH₂OCH₃ CF₃ H H A-577 I.1A CH₃OCH₂CH₂OCH₃ CHF₂ H H A-578 I.1A CH₃ OCH₂CH₂OCH₃ OCH₃ H H A-579 I.1A CH₃OCH₂CH₂OCH₃ OCHF₂ H H A-580 I.1A CH₃ OCH₂CH₂OCH₃ SCH₃ H H A-581 I.1A CH₃SO₂CH₃ H H H A-582 I.1A CH₃ SO₂CH₃ CH₃ H H A-583 I.1A CH₃ SO₂CH₃ CF₃ H HA-584 I.1A CH₃ SO₂CH₃ CHF₂ H H A-585 I.1A CH₃ SO₂CH₃ OCH₃ H H A-586 I.1ACH₃ SO₂CH₃ OCHF₂ H H A-587 I.1A CH₃ SO₂CH₃ SCH₃ H H A-588 I.1A CH₃SO₂CH₂CH₃ H H H A-589 I.1A CH₃ SO₂CH₂CH₃ CH₃ H H A-590 I.1A CH₃SO₂CH₂CH₃ CF₃ H H A-591 I.1A CH₃ SO₂CH₂CH₃ CHF₂ H H A-592 I.1A CH₃SO₂CH₂CH₃ OCH₃ H H A-593 I.1A CH₃ SO₂CH₂CH₃ OCHF₂ H H A-594 I.1A CH₃SO₂CH₂CH₃ SCH₃ H H A-595 I.1A CH₃ SO₂CH(CH₃)₂ H H H A-596 I.1A CH₃SO₂CH(CH₃)₂ CH₃ H H A-597 I.1A CH₃ SO₂CH(CH₃)₂ CF₃ H H A-598 I.1A CH₃SO₂CH(CH₃)₂ CHF₂ H H A-599 I.1A CH₃ SO₂CH(CH₃)₂ OCH₃ H H A-600 I.1A CH₃SO₂CH(CH₃)₂ OCHF₂ H H A-601 I.1A CH₃ SO₂CH(CH₃)₂ SCH₃ H H A-602 I.1A CH₃COOCH₃ H H H A-603 I.1A CH₃ COOCH₃ CH₃ H H A-604 I.1A CH₃ COOCH₃ CF₃ H HA-605 I.1A CH₃ COOCH₃ CHF₂ H H A-606 I.1A CH₃ COOCH₃ OCH₃ H H A-607 I.1ACH₃ COOCH₃ OCHF₂ H H A-608 I.1A CH₃ COOCH₃ SCH₃ H H A-609 I.1A CH₃COOCH₂CH₃ H H H A-610 I.1A CH₃ COOCH₂CH₃ CH₃ H H A-611 I.1A CH₃COOCH₂CH₃ CF₃ H H A-612 I.1A CH₃ COOCH₂CH₃ CHF₂ H H A-613 I.1A CH₃COOCH₂CH₃ OCH₃ H H A-614 I.1A CH₃ COOCH₂CH₃ OCHF₂ H H A-615 I.1A CH₃COOCH₂CH₃ SCH₃ H H A-616 I.1A CH₃ #²-CH₂CH₂SO₂-#³ H H A-617 I.1A CH₃#²-CH(CH₃)CH₂SO₂-#³ H H A-618 I.1A CH₃ #²-C(CH₃)₂CH₂SO₂-#³ H H A-619I.1A CH₃ #²-SO₂CH₂CH₂SO₂-#³ H H A-620 I.1A CH₃#²-CH(OCH₂CH₂F)CH₂CH₂SO₂-#³ H H A-621 I.1A CH₃ #²-C(═NOCH₃)CH₂CH₂SO₂-#³H H A-622 I.1A CH₃ #²-SO₂CH₂CH₂C(CH₃)₂-#³ H H A-623 I.1A CH₃#²-N(CH₃)C(═O)S-#³ H H A-624 I.1A CH₃ #²-C(═O)N(CH₃)SO₂-#³ H H A-625I.1A CF₃

H H H A-626 I.1A CF₃

CH₃ H H A-627 I.1A CF₃

CF₃ H H A-628 I.1A CF₃

CHF₂ H H A-629 I.1A CF₃

OCH₃ H H A-630 I.1A CF₃

OCHF₂ H H A-631 I.1A CF₃

SCH₃ H H A-632 I.1A CF₃

H H H A-633 I.1A CF₃

CH₃ H H A-634 I.1A CF₃

CF₃ H H A-635 I.1A CF₃

CHF₂ H H A-636 I.1A CF₃

OCH₃ H H A-637 I.1A CF₃

OCHF₂ H H A-638 I.1A CF₃

SCH₃ H H A-639 I.1A CF₃

H H H A-640 I.1A CF₃

CH₃ H H A-641 I.1A CF₃

CF₃ H H A-642 I.1A CF₃

CHF₂ H H A-643 I.1A CF₃

OCH₃ H H A-644 I.1A CF₃

OCHF₂ H H A-645 I.1A CF₃

SCH₃ H H A-646 I.1A CF₃

H H H A-647 I.1A CF₃

CH₃ H H A-648 I.1A CF₃

CF₃ H H A-649 I.1A CF₃

CHF₂ H H A-650 I.1A CF₃

OCH₃ H H A-651 I.1A CF₃

OCHF₂ H H A-652 I.1A CF₃

SCH₃ H H A-653 I.1A CF₃

H H H A-654 I.1A CF₃

CH₃ H H A-655 I.1A CF₃

CF₃ H H A-656 I.1A CF₃

CHF₂ H H A-657 I.1A CF₃

OCH₃ H H A-658 I.1A CF₃

OCHF₂ H H A-659 I.1A CF₃

SCH₃ H H A-660 I.1A CF₃

H H H A-661 I.1A CF₃

CH₃ H H A-662 I.1A CF₃

CF₃ H H A-663 I.1A CF₃

CHF₂ H H A-664 I.1A CF₃

OCH₃ H H A-665 I.1A CF₃

OCHF₂ H H A-666 I.1A CF₃

SCH₃ H H A-667 I.1A CF₃

H H H A-668 I.1A CF₃

CH₃ H H A-669 I.1A CF₃

CF₃ H H A-670 I.1A CF₃

CHF₂ H H A-671 I.1A CF₃

OCH₃ H H A-672 I.1A CF₃

OCHF₂ H H A-673 I.1A CF₃

SCH₃ H H A-674 I.1A CF₃

H H H A-675 I.1A CF₃

CH₃ H H A-676 I.1A CF₃

CF₃ H H A-677 I.1A CF₃

CHF₂ H H A-678 I.1A CF₃

OCH₃ H H A-679 I.1A CF₃

OCHF₂ H H A-680 I.1A CF₃

SCH₃ H H A-681 I.1A CF₃

H H H A-682 I.1A CF₃

CH₃ H H A-683 I.1A CF₃

CF₃ H H A-684 I.1A CF₃

CHF₂ H H A-685 I.1A CF₃

OCH₃ H H A-686 I.1A CF₃

OCHF₂ H H A-687 I.1A CF₃

SCH₃ H H A-688 I.1A CF₃

H H H A-689 I.1A CF₃

CH₃ H H A-690 I.1A CF₃

CF₃ H H A-691 I.1A CF₃

CHF₂ H H A-692 I.1A CF₃

OCH₃ H H A-693 I.1A CF₃

OCHF₂ H H A-694 I.1A CF₃

SCH₃ H H A-695 I.1A CF₃ C₆H₅ H H H A-696 I.1A CF₃ C₆H₅ CH₃ H H A-697I.1A CF₃ C₆H₅ CF₃ H H A-698 I.1A CF₃ C₆H₅ CHF₂ H H A-699 I.1A CF₃ C₆H₅OCH₃ H H A-700 I.1A CF₃ C₆H₅ OCHF₂ H H A-701 I.1A CF₃ C₆H5 SCH₃ H HA-702 I.1A CF₃ 4-OCH₃—C₆H₄ H H H A-703 I.1A CF₃ 4-OCH₃—C₆H₄ CH₃ H HA-704 I.1A CF₃ 4-OCH₃—C₆H₄ CF₃ H H A-705 I.1A CF₃ 4-OCH₃—C₆H₄ CHF₂ H HA-706 I.1A CF₃ 4-OCH₃—C₆H₄ OCH₃ H H A-707 I.1A CF₃ 4-OCH₃—C₆H₄ OCHF₂ H HA-708 I.1A CF₃ 4-OCH₃—C₆H4 SCH₃ H H A-709 I.1A CF₃ CH═CH₂ H H H A-710I.1A CF₃ CH═CH₂ CH₃ H H A-711 I.1A CF₃ CH═CH₂ CF₃ H H A-712 I.1A CF₃CH═CH₂ CHF₂ H H A-713 I.1A CF₃ CH═CH₂ OCH₃ H H A-714 I.1A CF₃ CH═CH₂OCHF₂ H H A-715 I.1A CF₃ CH═CH₂ SCH₃ H H A-716 I.1A CF₃ CH═CH—CH₃ H H HA-717 I.1A CF₃ CH═CH—CH₃ CH₃ H H A-718 I.1A CF₃ CH═CH—CH₃ CF₃ H H A-719I.1A CF₃ CH═CH—CH₃ CHF₂ H H A-720 I.1A CF₃ CH═CH—CH₃ OCH₃ H H A-721 I.1ACF₃ CH═CH—CH₃ OCHF₂ H H A-722 I.1A CF₃ CH═CH—CH₃ SCH₃ H H A-723 I.1A CF₃CH₂CH═CH₂ H H H A-724 I.1A CF₃ CH₂CH═CH₂ CH₃ H H A-725 I.1A CF₃CH₂CH═CH₂ CF₃ H H A-726 I.1A CF₃ CH₂CH═CH₂ CHF₂ H H A-727 I.1A CF₃CH₂CH═CH₂ OCH₃ H H A-728 I.1A CF₃ CH₂CH═CH₂ OCHF₂ H H A-729 I.1A CF₃CH₂CH═CH₂ SCH₃ H H A-730 I.1A CF₃ CH₂C≡ CH H H H A-731 I.1A CF₃ CH₂C≡ CHCH₃ H H A-732 I.1A CF₃ CH₂C≡ CH CF₃ H H A-733 I.1A CF₃ CH₂C≡ CH CHF₂ H HA-734 I.1A CF₃ CH₂C≡ CH OCH₃ H H A-735 I.1A CF₃ CH₂C≡ CH OCHF₂ H H A-736I.1A CF₃ CH₂C≡ CH SCH₃ H H A-737 I.1A CF₃ CH₂OCH₂CF₃ H H H A-738 I.1ACF₃ CH₂OCH₂CF₃ CH₃ H H A-739 I.1A CF₃ CH₂OCH₂CF₃ CF₃ H H A-740 I.1A CF₃CH₂OCH₂CF₃ CHF₂ H H A-741 I.1A CF₃ CH₂OCH₂CF₃ OCH₃ H H A-742 I.1A CF₃CH₂OCH₂CF₃ OCHF₂ H H A-743 I.1A CF₃ CH₂OCH₂CF₃ SCH₃ H H A-744 I.1A CF₃

H H H A-745 I.1A CF₃

CH₃ H H A-746 I.1A CF₃

CF₃ H H A-747 I.1A CF₃

CHF₂ H H A-748 I.1A CF₃

OCH₃ H H A-749 I.1A CF₃

OCHF₂ H H A-750 I.1A CF₃

SCH₃ H H A-751 I.1A CF₃ OCH₂CH₃ H H H A-752 I.1A CF₃ OCH₂CH₃ CH₃ H HA-753 I.1A CF₃ OCH₂CH₃ CF₃ H H A-754 I.1A CF₃ OCH₂CH₃ CHF₂ H H A-755I.1A CF₃ OCH₂CH₃ OCH₃ H H A-756 I.1A CF₃ OCH₂CH₃ OCHF₂ H H A-757 I.1ACF₃ OCH₂CH₃ SCH₃ H H A-758 I.1A CF₃ OCH₂CH₂OCH₃ H H H A-759 I.1A CF₃OCH₂CH₂OCH₃ CH₃ H H A-760 I.1A CF₃ OCH₂CH₂OCH₃ CF₃ H H A-761 I.1A CF₃OCH₂CH₂OCH₃ CHF₂ H H A-762 I.1A CF₃ OCH₂CH₂OCH₃ OCH₃ H H A-763 I.1A CF₃OCH₂CH₂OCH₃ OCHF₂ H H A-764 I.1A CF₃ OCH₂CH₂OCH₃ SCH₃ H H A-765 I.1A CF₃SO₂CH₃ H H H A-766 I.1A CF₃ SO₂CH₃ CH₃ H H A-767 I.1A CF₃ SO₂CH₃ CF₃ H HA-768 I.1A CF₃ SO₂CH₃ CHF₂ H H A-769 I.1A CF₃ SO₂CH₃ OCH₃ H H A-770 I.1ACF₃ SO₂CH₃ OCHF₂ H H A-771 I.1A CF₃ SO₂CH₃ SCH₃ H H A-772 I.1A CF₃SO₂CH₂CH₃ H H H A-773 I.1A CF₃ SO₂CH₂CH₃ CH₃ H H A-774 I.1A CF₃SO₂CH₂CH₃ CF₃ H H A-775 I.1A CF₃ SO₂CH₂CH₃ CHF₂ H H A-776 I.1A CF₃SO₂CH₂CH₃ OCH₃ H H A-777 I.1A CF₃ SO₂CH₂CH₃ OCHF₂ H H A-778 I.1A CF₃SO₂CH₂CH₃ SCH₃ H H A-779 I.1A CF₃ SO₂CH(CH₃)₂ H H H A-780 I.1A CF₃SO₂CH(CH₃)₂ CH₃ H H A-781 I.1A CF₃ SO₂CH(CH₃)₂ CF₃ H H A-782 I.1A CF₃SO₂CH(CH₃)₂ CHF₂ H H A-783 I.1A CF₃ SO₂CH(CH₃)₂ OCH₃ H H A-784 I.1A CF₃SO₂CH(CH₃)₂ OCHF₂ H H A-785 I.1A CF₃ SO₂CH(CH₃)₂ SCH₃ H H A-786 I.1A CF₃COOCH₃ H H H A-787 I.1A CF₃ COOCH₃ CH₃ H H A-788 I.1A CF₃ COOCH₃ CF₃ H HA-789 I.1A CF₃ COOCH₃ CHF₂ H H A-790 I.1A CF₃ COOCH₃ OCH₃ H H A-791 I.1ACF₃ COOCH₃ OCHF₂ H H A-792 I.1A CF₃ COOCH₃ SCH₃ H H A-793 I.1A CF₃COOCH₂CH₃ H H H A-794 I.1A CF₃ COOCH₂CH₃ CH₃ H H A-795 I.1A CF₃COOCH₂CH₃ CF₃ H H A-796 I.1A CF₃ COOCH₂CH₃ CHF₂ H H A-797 I.1A CF₃COOCH₂CH₃ OCH₃ H H A-798 I.1A CF₃ COOCH₂CH₃ OCHF₂ H H A-799 I.1A CF₃COOCH₂CH₃ SCH₃ H H A-800 I.1A CF₃ #²-CH₂CH₂SO₂-#³ H H A-801 I.1A CF₃#²-CH(CH₃)CH₂SO₂-#³ H H A-802 I.1A CF₃ #²-C(CH₃)₂CH₂SO₂-#³ H H A-803I.1A CF₃ #²-SO₂CH₂CH₂SO₂-#³ H H A-804 I.1A CF₃#²-CH(OCH₂CH₂F)CH₂CH₂SO₂-#³ H H A-805 I.1A CF₃ #²-C(═NOCH₃)CH₂CH₂SO₂-#³H H A-806 I.1A CF₃ #²-SO₂CH₂CH₂C(CH₃)₂-#³ H H A-807 I.1A CF₃#²-N(CH₃)C(═O)S-#³ H H A-808 I.1A CF₃ #²-C(═O)N(CH₃)SO₂-#³ H H A-809I.1A OCF₃

H H H A-810 I.1A OCF₃

CH₃ H H A-811 I.1A OCF₃

CF₃ H H A-812 I.1A OCF₃

CHF₂ H H A-813 I.1A OCF₃

OCH₃ H H A-814 I.1A OCF₃

OCHF₂ H H A-815 I.1A OCF₃

SCH₃ H H A-816 I.1A OCF₃

H H H A-817 I.1A OCF₃

CH₃ H H A-818 I.1A OCF₃

CF₃ H H A-819 I.1A OCF₃

CHF₂ H H A-820 I.1A OCF₃

OCH₃ H H A-821 I.1A OCF₃

OCHF₂ H H A-822 I.1A OCF₃

SCH₃ H H A-823 I.1A OCF₃

H H H A-824 I.1A OCF₃

CH₃ H H A-825 I.1A OCF₃

CF₃ H H A-826 I.1A OCF₃

CHF₂ H H A-827 I.1A OCF₃

OCH₃ H H A-828 I.1A OCF₃

OCHF₂ H H A-829 I.1A OCF₃

SCH₃ H H A-830 I.1A OCF₃

H H H A-831 I.1A OCF₃

CH₃ H H A-832 I.1A OCF₃

CF₃ H H A-833 I.1A OCF₃

CHF₂ H H A-834 I.1A OCF₃

OCH₃ H H A-835 I.1A OCF₃

OCHF₂ H H A-836 I.1A OCF₃

SCH₃ H H A-837 I.1A OCF₃

H H H A-838 I.1A OCF₃

CH₃ H H A-839 I.1A OCF₃

CF₃ H H A-840 I.1A OCF₃

CHF₂ H H A-841 I.1A OCF₃

OCH₃ H H A-842 I.1A OCF₃

OCHF₂ H H A-843 I.1A OCF₃

SCH₃ H H A-844 I.1A OCF₃

H H H A-845 I.1A OCF₃

CH₃ H H A-846 I.1A OCF₃

CF₃ H H A-847 I.1A OCF₃

CHF₂ H H A-848 I.1A OCF₃

OCH₃ H H A-849 I.1A OCF₃

OCHF₂ H H A-850 I.1A OCF₃

SCH₃ H H A-851 I.1A OCF₃

H H H A-852 I.1A OCF₃

CH₃ H H A-853 I.1A OCF₃

CF₃ H H A-854 I.1A OCF₃

CHF₂ H H A-855 I.1A OCF₃

OCH₃ H H A-856 I.1A OCF₃

OCHF₂ H H A-857 I.1A OCF₃

SCH₃ H H A-858 I.1A OCF₃

H H H A-859 I.1A OCF₃

CH₃ H H A-860 I.1A OCF₃

CF₃ H H A-861 I.1A OCF₃

CHF₂ H H A-862 I.1A OCF₃

OCH₃ H H A-863 I.1A OCF₃

OCHF₂ H H A-864 I.1A OCF₃

SCH₃ H H A-865 I.1A OCF₃

H H H A-866 I.1A OCF₃

CH₃ H H A-867 I.1A OCF₃

CF₃ H H A-868 I.1A OCF₃

CHF₂ H H A-869 I.1A OCF₃

OCH₃ H H A-870 I.1A OCF₃

OCHF₂ H H A-871 I.1A OCF₃

SCH₃ H H A-872 I.1A OCF₃

H H H A-873 I.1A OCF₃

CH₃ H H A-874 I.1A OCF₃

CF₃ H H A-875 I.1A OCF₃

CHF₂ H H A-876 I.1A OCF₃

OCH₃ H H A-877 I.1A OCF₃

OCHF₂ H H A-878 I.1A OCF₃

SCH₃ H H A-879 I.1A OCF₃ C₆H₅ H H H A-880 I.1A OCF₃ C₆H₅ CH₃ H H A-881I.1A OCF₃ C₆H₅ CF₃ H H A-882 I.1A OCF₃ C₆H₅ CHF₂ H H A-883 I.1A OCF₃C₆H₅ OCH₃ H H A-884 I.1A OCF₃ C₆H₅ OCHF₂ H H A-885 I.1A OCF₃ C₆H₅ SCH₃ HH A-886 I.1A OCF₃ 4-OCH₃—C₆H₄ H H H A-887 I.1A OCF₃ 4-OCH₃—C₆H₄ CH₃ H HA-888 I.1A OCF₃ 4-OCH₃—C₆H₄ CF₃ H H A-889 I.1A OCF₃ 4-OCH₃—C₆H₄ CHF₂ H HA-890 I.1A OCF₃ 4-OCH₃—C₆H₄ OCH₃ H H A-891 I.1A OCF₃ 4-OCH₃—C₆H₄ OCHF₂ HH A-892 I.1A OCF₃ 4-OCH₃—C₆H₄ SCH₃ H H A-893 I.1A OCF₃ CH═CH₂ H H HA-894 I.1A OCF₃ CH═CH₂ CH₃ H H A-895 I.1A OCF₃ CH═CH₂ CF₃ H H A-896 I.1AOCF₃ CH═CH₂ CHF₂ H H A-897 I.1A OCF₃ CH═CH₂ OCH₃ H H A-898 I.1A OCF₃CH═CH₂ OCHF₂ H H A-899 I.1A OCF₃ CH═CH₂ SCH₃ H H A-900 I.1A OCF₃CH═CH—CH₃ H H H A-901 I.1A OCF₃ CH═CH—CH₃ CH₃ H H A-902 I.1A OCF₃CH═CH—CH₃ CF₃ H H A-903 I.1A OCF₃ CH═CH—CH₃ CHF₂ H H A-904 I.1A OCF₃CH═CH—CH₃ OCH₃ H H A-905 I.1A OCF₃ CH═CH—CH₃ OCHF₂ H H A-906 I.1A OCF₃CH═CH—CH₃ SCH₃ H H A-907 I.1A OCF₃ CH₂CH═CH₂ H H H A-908 I.1A OCF₃CH₂CH═CH₂ CH₃ H H A-909 I.1A OCF₃ CH₂CH═CH₂ CF₃ H H A-910 I.1A OCF₃CH₂CH═CH₂ CHF₂ H H A-911 I.1A OCF₃ CH₂CH═CH₂ OCHF₂ H H A-912 I.1A OCF₃CH₂CH═CH₂ OCHF₂ H H A-913 I.1A OCF₃ CH₂CH═CH₂ SCH₃ H H A-914 I.1A OCF₃CH₂C≡ CH H H H A-915 I.1A OCF₃ CH₂C≡ CH CF₃ H H A-916 I.1A OCF₃ CH₂C≡ CHCF₃ H H A-917 I.1A OCF₃ CH₂C≡ CH OCH₃ H H A-918 I.1A OCF₃ CH₂C≡ CH OCH₃H H A-919 I.1A OCF₃ CH₂C≡ CH OCHF₂ H H A-920 I.1A OCF₃ CH₂C≡ CH SCH₃ H HA-921 I.1A OCF₃ CH₂OCH₂CF₃ H H H A-922 I.1A OCF₃ CH₂OCH₂CF₃ CH₃ H HA-923 I.1A OCF₃ CH₂OCH₂CF₃ CF₃ H H A-924 I.1A OCF₃ CH₂OCH₂CF₃ CHF₂ H HA-925 I.1A OCF₃ CH₂OCH₂CF₃ OCH₃ H H A-926 I.1A OCF₃ CH₂OCH₂CF₃ OCHF₂ H HA-927 I.1A OCF₃ CH₂OCH₂CF₃ SCH₃ H H A-928 I.1A OCF₃

H H H A-929 I.1A OCF₃

CH₃ H H A-930 I.1A OCF₃

CF₃ H H A-931 I.1A OCF₃

CHF₂ H H A-932 I.1A OCF₃

OCH₃ H H A-933 I.1A OCF₃

OCHF₂ H H A-934 I.1A OCF₃

SCH₃ H H A-935 I.1A OCF₃ OCH₂CH₃ H H H A-936 I.1A OCF₃ OCH₂CH₃ CH₃ H HA-937 I.1A OCF₃ OCH₂CH₃ CF₃ H H A-938 I.1A OCF₃ OCH₂CH₃ CHF₂ H H A-939I.1A OCF₃ OCH₂CH₃ OCH₃ H H A-940 I.1A OCF₃ OCH₂CH₃ OCHF₂ H H A-941 I.1AOCF₃ OCH₂CH₃ SCH₃ H H A-942 I.1A OCF₃ OCH₂CH₂OCH₃ H H H A-943 I.1A OCF₃OCH₂CH₂OCH₃ CH₃ H H A-944 I.1A OCF₃ OCH₂CH₂OCH₃ CF₃ H H A-945 I.1A OCF₃OCH₂CH₂OCH₃ CHF₂ H H A-946 I.1A OCF₃ OCH₂CH₂OCH₃ OCH₃ H H A-947 I.1AOCF₃ OCH₂CH₂OCH₃ OCHF₂ H H A-948 I.1A OCF₃ OCH₂CH₂OCH₃ SCH₃ H H A-949I.1A OCF₃ SO₂CH₃ H H H A-950 I.1A OCF₃ SO₂CH₃ CH₃ H H A-951 I.1A OCF₃SO₂CH₃ CF₃ H H A-952 I.1A OCF₃ SO₂CH₃ CHF₂ H H A-953 I.1A OCF₃ SO₂CH₃OCH₃ H H A-954 I.1A OCF₃ SO₂CH₃ OCHF₂ H H A-955 I.1A OCF₃ SO₂CH₃ SCH₃ HH A-956 I.1A OCF₃ SO₂CH₂CH₃ H H H A-957 I.1A OCF₃ SO₂CH₂CH₃ CH₃ H HA-958 I.1A OCF₃ SO₂CH₂CH₃ CF₃ H H A-959 I.1A OCF₃ SO₂CH₂CH₃ CHF₂ H HA-960 I.1A OCF₃ SO₂CH₂CH₃ OCH₃ H H A-961 I.1A OCF₃ SO₂CH₂CH₃ OCHF₂ H HA-962 I.1A OCF₃ SO₂CH₂CH₃ SCH₃ H H A-963 I.1A OCF₃ SO₂CH(CH₃)₂ H H HA-964 I.1A OCF₃ SO₂CH(CH₃)₂ CH₃ H H A-965 I.1A OCF₃ SO₂CH(CH₃)₂ CF₃ H HA-966 I.1A OCF₃ SO₂CH(CH₃)₂ CHF₂ H H A-967 I.1A OCF₃ SO₂CH(CH₃)₂ OCH₃ HH A-968 I.1A OCF₃ SO₂CH(CH₃)₂ OCHF₂ H H A-969 I.1A OCF₃ SO₂CH(CH₃)₂ SCH₃H H A-970 I.1A OCF₃ COOCH₃ H H H A-971 I.1A OCF₃ COOCH₃ CH₃ H H A-972I.1A OCF₃ COOCH₃ CF₃ H H A-973 I.1A OCF₃ COOCH₃ CHF₂ H H A-974 I.1A OCF₃COOCH₃ OCH₃ H H A-975 I.1A OCF₃ COOCH₃ OCHF₂ H H A-976 I.1A OCF₃ COOCH₃SCH₃ H H A-977 I.1A OCF₃ COOCH₂CH₃ H H H A-978 I.1A OCF₃ COOCH₂CH₃ CH₃ HH A-979 I.1A OCF₃ COOCH₂CH₃ CF₃ H H A-980 I.1A OCF₃ COOCH₂CH₃ CHF₂ H HA-981 I.1A OCF₃ COOCH₂CH₃ OCH₃ H H A-982 I.1A OCF₃ COOCH₂CH₃ OCHF₂ H HA-983 I.1A OCF₃ COOCH₂CH₃ SCH₃ H H A-984 I.1A OCF₃ #²-CH₂CH₂SO₂-#³ H HA-985 I.1A OCF₃ #²-CH(CH₃)CH₂SO₂-#³ H H A-986 I.1A OCF₃#²-C(CH₃)₂CH₂SO₂-#³ H H A-987 I.1A OCF₃ #²-SO₂CH₂CH₂SO₂-#³ H H A-988I.1A OCF₃ #²-CH(OCH₂CH₂F)CH₂CH₂SO₂-#³ H H A-989 I.1A OCF₃#²-C(═NOCH₃)CH₂CH₂SO₂-#³ H H A-990 I.1A OCF₃ #²-SO₂CH₂CH₂C(CH₃)₂-#³ H HA-991 I.1A OCF₃ #²-N(CH₃)C(═O)S-#³ H H A-992 I.1A OCF₃#²-C(═O)N(CH₃)SO₂-#³ H H A-993 I.1A SCF₃

H H H A-994 I.1A SCF₃

CH₃ H H A-995 I.1A SCF₃

CF₃ H H A-996 I.1A SCF_(3/)

CHF₂ H H A-997 I.1A SCF₃

OCH₃ H H A-998 I.1A SCF₃

OCHF₂ H H A-999 I.1A SCF₃

SCH₃ H H A-1000 I.1A SCF₃

H H H A-1001 I.1A SCF₃

CH₃ H H A-1002 I.1A SCF₃

CF₃ H H A-1003 I.1A SCF₃

CHF₂ H H A-1004 I.1A SCF₃

OCH₃ H H A-1005 I.1A SCF₃

OCHF₂ H H A-1006 I.1A SCF₃

SCH₃ H H A-1007 I.1A SCF₃

H H H A-1008 I.1A SCF₃

CH₃ H H A-1009 I.1A SCF₃

CF₃ H H A-1010 I.1A SCF₃

CHF₂ H H A-1011 I.1A SCF₃

OCH₃ H H A-1012 I.1A SCF₃

OCHF₂ H H A-1013 I.1A SCF₃

SCH₃ H H A-1014 I.1A SCF₃

H H H A-1015 I.1A SCF₃

CH₃ H H A-1016 I.1A SCF₃

CF₃ H H A-1017 I.1A SCF₃

CHF₂ H H A-1018 I.1A SCF₃

OCH₃ H H A-1019 I.1A SCF₃

OCHF₂ H H A-1020 I.1A SCF₃

SCH₃ H H A-1021 I.1A SCF₃

H H H A-1022 I.1A SCF₃

CH₃ H H A-1023 I.1A SCF₃

CF₃ H H A-1024 I.1A SCF₃

CHF₂ H H A-1025 I.1A SCF₃

OCH₃ H H A-1026 I.1A SCF₃

OCHF₂ H H A-1027 I.1A SCF₃

SCH₃ H H A-1028 I.1A SCF₃

H H H A-1029 I.1A SCF₃

CH₃ H H A-1030 I.1A SCF₃

CF₃ H H A-1031 I.1A SCF₃

CHF₂ H H A-1032 I.1A SCF₃

OCH₃ H H A-1033 I.1A SCF₃

OCHF₂ H H A-1034 I.1A SCF₃

SCH₃ H H A-1035 I.1A SCF₃

H H H A-1036 I.1A SCF₃

CH₃ H H A-1037 I.1A SCF₃

CF₃ H H A-1038 I.1A SCF₃

CHF₂ H H A-1039 I.1A SCF₃

OCH₃ H H A-1040 I.1A SCF₃

OCHF₂ H H A-1041 I.1A SCF₃

SCH₃ H H A-1042 I.1A SCF₃

H H H A-1043 I.1A SCF₃

CH₃ H H A-1044 I.1A SCF₃

CF₃ H H A-1045 I.1A SCF₃

CHF₂ H H A-1046 I.1A SCF₃

OCH₃ H H A-1047 I.1A SCF₃

OCHF₂ H H A-1048 I.1A SCF₃

SCH₃ H H A-1049 I.1A SCF₃

H H H A-1050 I.1A SCF₃

CH₃ H H A-1051 I.1A SCF₃

CF₃ H H A-1052 I.1A SCF₃

CHF₂ H H A-1053 I.1A SCF₃

OCH₃ H H A-1054 I.1A SCF₃

OCHF₂ H H A-1055 I.1A SCF₃

SCH₃ H H A-1056 I.1A SCF₃

H H H A-1057 I.1A SCF₃

CH₃ H H A-1058 I.1A SCF₃

CF₃ H H A-1059 I.1A SCF₃

CHF₂ H H A-1060 I.1A SCF₃

OCH H H A-1061 I.1A SCF₃

OCHF₂ H H A-1062 I.1A SCF₃

SCH₃ H H A-1063 I.1A SCF₃ C₆H₅ H H H A-1064 I.1A SCF₃ C₆H₅ CH₃ H HA-1065 I.1A SCF₃ C₆H₅ CF₃ H H A-1066 I.1A SCF₃ C₆H₅ CHF₂ H H A-1067 I.1ASCF₃ C₆H₅ OCH₃ H H A-1068 I.1A SCF₃ C₆H₅ OCHF₂ H H A-1069 I.1A SCF₃ C₆H₅SCH₃ H H A-1070 I.1A SCF₃ 4-OCH₃—C₆H₄ H H H A-1071 I.1A SCF₃ 4-OCH₃—C₆H₄CH₃ H H A-1072 I.1A SCF₃ 4-OCH₃—C₆H₄ CF₃ H H A-1073 I.1A SCF₃4-OCH₃—C₆H₄ CHF₂ H H A-1074 I.1A SCF₃ 4-OCH₃—C₆H₄ OCH₃ H H A-1075 I.1ASCF₃ 4-OCH₃—C₆H₄ OCHF₂ H H A-1076 I.1A SCF₃ 4-OCH₃—C₆H₄ SCH₃ H H A-1077I.1A SCF₃ CH═CH₂ H H H A-1078 I.1A SCF₃ CH═CH₂ CH₃ H H A-1079 I.1A SCF₃CH═CH₂ CF₃ H H A-1080 I.1A SCF₃ CH═CH₂ CHF₂ H H A-1081 I.1A SCF₃ CH═CH₂OCH₃ H H A-1082 I.1A SCF₃ CH═CH₂ OCHF₂ H H A-1083 I.1A SCF₃ CH═CH₂ SCH₃H H A-1084 I.1A SCF₃ CH═CH—CH₃ H H H A-1085 I.1A SCF₃ CH═CH—CH₃ CH₃ H HA-1086 I.1A SCF₃ CH═CH—CH₃ CF₃ H H A-1087 I.1A SCF₃ CH═CH—CH₃ OCH₃ H HA-1088 I.1A SCF₃ CH═CH—CH₃ OCH₃ H H A-1089 I.1A SCF₃ CH═CH—CH₃ OCHF₂ H HA-1090 I.1A SCF₃ CH═CH—CH₃ SCH₃ H H A-1091 I.1A SCF₃ CH₂CH═CH₂ H H HA-1092 I.1A SCF₃ CH₂CH═CH₂ CH₃ H H A-1093 I.1A SCF₃ CH₂CH═CH₂ CF₃ H HA-1094 I.1A SCF₃ CH₂CH═CH₂ CHF₂ H H A-1095 I.1A SCF₃ CH₂CH═CH₂ OCH₃ H HA-1096 I.1A SCF₃ CH₂CH═CH₂ OCHF₂ H H A-1097 I.1A SCF₃ CH₂CH═CH₂ SCH₃ H HA-1098 I.1A SCF₃ CH₂C≡ CH H H H A-1099 I.1A SCF₃ CH₂C≡ CH CH₃ H H A-1100I.1A SCF₃ CH₂C≡ CH CF₃ H H A-1101 I.1A SCF₃ CH₂C≡ CH CHF₂ H H A-1102I.1A SCF₃ CH₂C≡ CH OCH₃ H H A-1103 I.1A SCF₃ CH₂C≡ CH OCHF₂ H H A-1104I.1A SCF₃ CH₂C≡ CH SCH₃ H H A-1105 I.1A SCF₃ CH₂OCH₂CF₃ H H H A-1106I.1A SCF₃ CH₂OCH₂CF₃ CH₃ H H A-1107 I.1A SCF₃ CH₂OCH₂CF₃ CF₃ H H A-1108I.1A SCF₃ CH₂OCH₂CF₃ CHF₂ H H A-1109 I.1A SCF₃ CH₂OCH₂CF₃ OCH₃ H HA-1110 I.1A SCF₃ CH₂OCH₂CF₃ OCHF₂ H H A-1111 I.1A SCF₃ CH₂OCH₂CF₃ SCH₃ HH A-1112 I.1A SCF₃

H H H A-1113 I.1A SCF₃

CH₃ H H A-1114 I.1A SCF₃

CF₃ H H A-1115 I.1A SCF₃

CHF₂ H H A-1116 I.1A SCF₃

OCH₃ H H A-1117 I.1A SCF₃

OCHF₂ H H A-1118 I.1A SCF₃

SCH₃ H H A-1119 I.1A SCF₃ OCH₂CH₃ H H H A-1120 I.1A SCF₃ OCH₂CH₃ CH₃ H HA-1121 I.1A SCF₃ OCH₂CH₃ CF₃ H H A-1122 I.1A SCF₃ OCH₂CH₃ CHF₂ H HA-1123 I.1A SCF₃ OCH₂CH₃ OCH₃ H H A-1124 I.1A SCF₃ OCH₂CH₃ OCHF₂ H HA-1125 I.1A SCF₃ OCH₂CH₃ SCH₃ H H A-1126 I.1A SCF₃ OCH₂CH₂OCH₃ H H HA-1127 I.1A SCF₃ OCH₂CH₂OCH₃ CH₃ H H A-1128 I.1A SCF₃ OCH₂CH₂OCH₃ CF₃ HH A-1129 I.1A SCF₃ OCH₂CH₂OCH₃ CHF₂ H H A-1130 I.1A SCF₃ OCH₂CH₂OCH₃OCH₃ H H A-1131 I.1A SCF₃ OCH₂CH₂OCH₃ OCHF₂ H H A-1132 I.1A SCF₃OCH₂CH₂OCH₃ SCH₃ H H A-1133 I.1A SCF₃ SO₂CH₃ H H H A-1134 I.1A SCF₃SO₂CH₃ CH₃ H H A-1135 I.1A SCF₃ SO₂CH₃ CF₃ H H A-1136 I.1A SCF₃ SO₂CH₃CHF₂ H H A-1137 I.1A SCF₃ SO₂CH₃ OCH₃ H H A-1138 I.1A SCF₃ SO₂CH₃ OCHF₂H H A-1139 I.1A SCF₃ SO₂CH₃ SCH₃ H H A-1140 I.1A SCF₃ SO₂CH₂CH₃ H H HA-1141 I.1A SCF₃ SO₂CH₂CH₃ CH₃ H H A-1142 I.1A SCF₃ SO₂CH₂CH₃ CF₃ H HA-1143 I.1A SCF₃ SO₂CH₂CH₃ CHF₂ H H A-1144 I.1A SCF₃ SO₂CH₂CH₃ OCH₃ H HA-1145 I.1A SCF₃ SO₂CH₂CH₃ OCHF₂ H H A-1146 I.1A SCF₃ SO₂CH₂CH₃ SCH₃ H HA-1147 I.1A SCF₃ SO₂CH(CH₃)₂ H H H A-1148 I.1A SCF₃ SO₂CH(CH₃)₂ CH₃ H HA-1149 I.1A SCF₃ SO₂CH(CH₃)₂ CF₃ H H A-1150 I.1A SCF₃ SO₂CH(CH₃)₂ CHF₂ HH A-1151 I.1A SCF₃ SO₂CH(CH₃)₂ OCH₃ H H A-1152 I.1A SCF₃ SO₂CH(CH₃)₂OCHF₂ H H A-1153 I.1A SCF₃ SO₂CH(CH₃)₂ SCH₃ H H A-1154 I.1A SCF₃ COOCH₃H H H A-1155 I.1A SCF₃ COOCH₃ CH₃ H H A-1156 I.1A SCF₃ COOCH₃ CF₃ H HA-1157 I.1A SCF₃ COOCH₃ CHF₂ H H A-1158 I.1A SCF₃ COOCH₃ OCH₃ H H A-1159I.1A SCF₃ COOCH₃ OCHF₂ H H A-1160 I.1A SCF₃ COOCH₃ SCH₃ H H A-1161 I.1ASCF₃ COOCH₂CH₃ H H H A-1162 I.1A SCF₃ COOCH₂CH₃ CH₃ H H A-1163 I.1A SCF₃COOCH₂CH₃ CF₃ H H A-1164 I.1A SCF₃ COOCH₂CH₃ CHF₂ H H A-1165 I.1A SCF₃COOCH₂CH₃ OCH₃ H H A-1166 I.1A SCF₃ COOCH₂CH₃ OCHF₂ H H A-1167 I.1A SCF₃COOCH₂CH₃ SCH₃ H H A-1168 I.1A SCF₃ #²-CH₂CH₂SO₂-#³ H H A-1169 I.1A SCF₃#²-CH(CH₃)CH₂SO₂-#³ H H A-1170 I.1A SCF₃ #²-C(CH₃)₂CH₂SO₂-#³ H H A-1171I.1A SCF₃ #²-SO₂CH₂CH₂SO₂-#³ H H A-1172 I.1A SCF₃#²-CH(OCH₂CH₂F)CH₂CH₂SO₂-#³ H H A-1173 I.1A SCF₃#²-C(═NOCH₃)CH₂CH₂SO₂-#³ H H A-1174 I.1A SCF₃ #²-SO₂CH₂CH₂C(CH₃)₂-#³ H HA-1175 I.1A SCF₃ #²-N(CH₃)C(═O)S-#³ H H A-1176 I.1A SCF₃#²-C(═O)N(CH₃)SO₂-#³ H H A-1177 1.2A CH₂OCH₂CH₂OCH₃ — CF₃ H H A-1178I.1A #¹-CH═CH—CH═N-#² F H H A-1179 I.1A #¹-CH═CH—CH═N-#² Cl H H A-1180I.1A #¹-CH═CH—CH═N-#² CF₃ H H #¹characterizes the bond in position 2(group R¹) #²characterizes the bond in position 3 (group R²)#³characterizes the bond in position 4 (group R³)

Table A.1

Also especially preferred are compounds A.1-7 to A.1-18, A.1-37 toA.1-72, A.1-73, A.1-80, A.1-87, A.1-94, A.1-101, A.1-108, A.1-115,A.1-122, A.1-129, A.1-136, A.1-143, A.1-150, A.1-157, A.1-164, A.1-171,A.1-178, A.1-185, A.1-192, A.1-199, A.1-206, A.1-213, A.1-220, A.1-227,A.1-234, A.1-241, A.1-257, A.1-264, A.1-271, A.1-278, A.1-285, A.1-292,A.1-299, A.1-306, A.1-313, A.1-320, A.1-327, A.1-334, A.1-341, A.1-348,A.1-355, A.1-362, A.1-369, A.1-376, A.1-383, A.1-390, A.1-397, A.1-404,A.1-411, A.1-418, A.1-425, A.1-441, A.1-448, A.1-455, A.1-462, A.1-469,A.1-476, A.1-483, A.1-490, A.1-497, A.1-504, A.1-511, A.1-518, A.1-525,A.1-532, A.1-539, A.1-546, A.1-553, A.1-560, A.1-567, A.1-574, A.1-581,A.1-588, A.1-595, A.1-602, A.1-609, A.1-625, A.1-632, A.1-639, A.1-646,A.1-653, A.1-660, A.1-667, A.1-674, A.1-681, A.1-688, A.1-695, A.1-702,A.1-709, A.1-716, A.1-723, A.1-730, A.1-737, A.1-744, A.1-751, A.1-758,A.1-765, A.1-772, A.1-779, A.1-786, A.1-793, A.1-809, A.1-816, A.1-823,A.1-830, A.1-837, A.1-844, A.1-851, A.1-858, A.1-865, A.1-872, A.1-879,A.1-886, A.1-893, A.1-900, A.1-907, A.1-914, A.1-921, A.1-928, A.1-935,A.1-942, A.1-949, A.1-956, A.1-963, A.1-970, A.1-977, A.1-993, A.1-1000,A.1-1007, A.1-1014, A.1-1021, A.1-1028, A.1-1035, A.1-1042, A.1-1049,A.1-1056, A.1-1063, A.1-1070, A.1-1077, A.1-1084, A.1-1091, A.1-1098,A.1-1105, A.1-1112, A.1-1119, A.1-1126, A.1-1133, A.1-1140, A.1-1147,A.1-1154, A.1-1161 and A.1-1177 which differ from the correspondingcompounds A-7 to A-18, A-37 to A-72, A-73, A-80, A-87, A-94, A-101,A-108, A-115, A-122, A-129, A-136, A-143, A-150, A-157, A-164, A-171,A-178, A-185, A-192, A-199, A-206, A-213, A-220, A-227, A-234, A-241,A-257, A-264, A-271, A-278, A-285, A-292, A-299, A-306, A-313, A-320,A-327, A-334, A-341, A-348, A-355, A-362, A-369, A-376, A-383, A-390,A-397, A-404, A-411, A-418, A-425, A-441, A-448, A-455, A-462, A-469,A-476, A-483, A-490, A-497, A-504, A-511, A-518, A-525, A-532, A-539,A-546, A-553, A-560, A-567, A-574, A-581, A-588, A-595, A-602, A-609,A-625, A-632, A-639, A-646, A-653, A-660, A-667, A-674, A-681, A-688,A-695, A-702, A-709, A-716, A-723, A-730, A-737, A-744, A-751, A-758,A-765, A-772, A-779, A-786, A-793, A-809, A-816, A-823, A-830, A-837,A-844, A-851, A-858, A-865, A-872, A-879, A-886, A-893, A-900, A-907,A-914, A-921, A-928, A-935, A-942, A-949, A-956, A-963, A-970, A-977,A-993, A-1000, A-1007, A-1014, A-1021, A-1028, A-1035, A-1042, A-1049,A-1056, A-1063, A-1070, A-1077, A-1084, A-1091, A-1098, A-1105, A-1112,A-1119, A-1126, A-1133, A-1140, A-1147, A-1154, A-1161 and A-1177 onlyin that R³ is F.

Table A.2

Also especially preferred are compounds A.2-7 to A.2-18, A.2-37 toA.2-72, A.2-73, A.2-80, A.2-87, A.2-94, A.2-101, A.2-108, A.2-115,A.2-122, A.2-129, A.2-136, A.2-143, A.2-150, A.2-157, A.2-164, A.2-171,A.2-178, A.2-185, A.2-192, A.2-199, A.2-206, A.2-213, A.2-220, A.2-227,A.2-234, A.2-241, A.2-257, A.2-264, A.2-271, A.2-278, A.2-285, A.2-292,A.2-299, A.2-306, A.2-313, A.2-320, A.2-327, A.2-334, A.2-341, A.2-348,A.2-355, A.2-362, A.2-369, A.2-376, A.2-383, A.2-390, A.2-397, A.2-404,A.2-411, A.2-418, A.2-425, A.2-441, A.2-448, A.2-455, A.2-462, A.2-469,A.2-476, A.2-483, A.2-490, A.2-497, A.2-504, A.2-511, A.2-518, A.2-525,A.2-532, A.2-539, A.2-546, A.2-553, A.2-560, A.2-567, A.2-574, A.2-581,A.2-588, A.2-595, A.2-602, A.2-609, A.2-625, A.2-632, A.2-639, A.2-646,A.2-653, A.2-660, A.2-667, A.2-674, A.2-681, A.2-688, A.2-695, A.2-702,A.2-709, A.2-716, A.2-723, A.2-730, A.2-737, A.2-744, A.2-751, A.2-758,A.2-765, A.2-772, A.2-779, A.2-786, A.2-793, A.2-809, A.2-816, A.2-823,A.2-830, A.2-837, A.2-844, A.2-851, A.2-858, A.2-865, A.2-872, A.2-879,A.2-886, A.2-893, A.2-900, A.2-907, A.2-914, A.2-921, A.2-928, A.2-935,A.2-942, A.2-949, A.2-956, A.2-963, A.2-970, A.2-977, A.2-993, A.2-1000,A.2-1007, A.2-1014, A.2-1021, A.2-1028, A.2-1035, A.2-1042, A.2-1049,A.2-1056, A.2-1063, A.2-1070, A.2-1077, A.2-1084, A.2-1091, A.2-1098,A.2-1105, A.2-1112, A.2-1119, A.2-1126, A.2-1133, A.2-1140, A.2-1147,A.2-1154, A.2-1161 and A.2-1177 which differ from the correspondingcompounds A-7 to A-18, A-37 to A-72, A-73, A-80, A-87, A-94, A-101,A-108, A-115, A-122, A-129, A-136, A-143, A-150, A-157, A-164, A-171,A-178, A-185, A-192, A-199, A-206, A-213, A-220, A-227, A-234, A-241,A-257, A-264, A-271, A-278, A-285, A-292, A-299, A-306, A-313, A-320,A-327, A-334, A-341, A-348, A-355, A-362, A-369, A-376, A-383, A-390,A-397, A-404, A-411, A-418, A-425, A-441, A-448, A-455, A-462, A-469,A-476, A-483, A-490, A-497, A-504, A-511, A-518, A-525, A-532, A-539,A-546, A-553, A-560, A-567, A-574, A-581, A-588, A-595, A-602, A-609,A-625, A-632, A-639, A-646, A-653, A-660, A-667, A-674, A-681, A-688,A-695, A-702, A-709, A-716, A-723, A-730, A-737, A-744, A-751, A-758,A-765, A-772, A-779, A-786, A-793, A-809, A-816, A-823, A-830, A-837,A-844, A-851, A-858, A-865, A-872, A-879, A-886, A-893, A-900, A-907,A-914, A-921, A-928, A-935, A-942, A-949, A-956, A-963, A-970, A-977,A-993, A-1000, A-1007, A-1014, A-1021, A-1028, A-1035, A-1042, A-1049,A-1056, A-1063, A-1070, A-1077, A-1084, A-1091, A-1098, A-1105, A-1112,A-1119, A-1126, A-1133, A-1140, A-1147, A-1154, A-1161 and A-1177 onlyin that R³ is Cl.

Table A.3

Also especially preferred are compounds A.3-1 to A.3-54 and A.3-73 toA.3-1180 which differ from the corresponding compounds A-1 to A-54 andA-73 to A-1180 only in that R⁵ is F.

Table A.4

Also especially preferred are compounds A.4-1 to A.4-54 and A.4-67 toA.4-1180 which differ from the corresponding compounds A-1 to A-54 andA-67 to A-1180 only in that R⁵ is Cl.

Table A.5

Also especially preferred are compounds A.5-7 to A.5-18, A.5-37 toA.5-72, A.5-73, A.5-80, A.5-87, A.5-94, A.5-101, A.5-108, A.5-115,A.5-122, A.5-129, A.5-136, A.5-143, A.5-150, A.5-157, A.5-164, A.5-171,A.5-178, A.5-185, A.5-192, A.5-199, A.5-206, A.5-213, A.5-220, A.5-227,A.5-234, A.5-241, A.5-257, A.5-264, A.5-271, A.5-278, A.5-285, A.5-292,A.5-299, A.5-306, A.5-313, A.5-320, A.5-327, A.5-334, A.5-341, A.5-348,A.5-355, A.5-362, A.5-369, A.5-376, A.5-383, A.5-390, A.5-397, A.5-404,A.5-411, A.5-418, A.5-425, A.5-441, A.5-448, A.5-455, A.5-462, A.5-469,A.5-476, A.5-483, A.5-490, A.5-497, A.5-504, A.5-511, A.5-518, A.5-525,A.5-532, A.5-539, A.5-546, A.5-553, A.5-560, A.5-567, A.5-574, A.5-581,A.5-588, A.5-595, A.5-602, A.5-609, A.5-625, A.5-632, A.5-639, A.5-646,A.5-653, A.5-660, A.5-667, A.5-674, A.5-681, A.5-688, A.5-695, A.5-702,A.5-709, A.5-716, A.5-723, A.5-730, A.5-737, A.5-744, A.5-751, A.5-758,A.5-765, A.5-772, A.5-779, A.5-786, A.5-793, A.5-809, A.5-816, A.5-823,A.5-830, A.5-837, A.5-844, A.5-851, A.5-858, A.5-865, A.5-872, A.5-879,A.5-886, A.5-893, A.5-900, A.5-907, A.5-914, A.5-921, A.5-928, A.5-935,A.5-942, A.5-949, A.5-956, A.5-963, A.5-970, A.5-977, A.5-993, A.5-1000,A.5-1007, A.5-1014, A.5-1021, A.5-1028, A.5-1035, A.5-1042, A.5-1049,A.5-1056, A.5-1063, A.5-1070, A.5-1077, A.5-1084, A.5-1091, A.5-1098,A.5-1105, A.5-1112, A.5-1119, A.5-1126, A.5-1133, A.5-1140, A.5-1147,A.5-1154, A.5-1161 and A.5-1177 which differ from the correspondingcompounds A.1-7 to A.1-18, A.1-37 to A.1-72, A.1-73, A.1-80, A.1-87,A.1-94, A.1-101, A.1-108, A.1-115, A.1-122, A.1-129, A.1-136, A.1-143,A.1-150, A.1-157, A.1-164, A.1-171, A.1-178, A.1-185, A.1-192, A.1-199,A.1-206, A.1-213, A.1-220, A.1-227, A.1-234, A.1-241, A.1-257, A.1-264,A.1-271, A.1-278, A.1-285, A.1-292, A.1-299, A.1-306, A.1-313, A.1-320,A.1-327, A.1-334, A.1-341, A.1-348, A.1-355, A.1-362, A.1-369, A.1-376,A.1-383, A.1-390, A.1-397, A.1-404, A.1-411, A.1-418, A.1-425, A.1-441,A.1-448, A.1-455, A.1-462, A.1-469, A.1-476, A.1-483, A.1-490, A.1-497,A.1-504, A.1-511, A.1-518, A.1-525, A.1-532, A.1-539, A.1-546, A.1-553,A.1-560, A.1-567, A.1-574, A.1-581, A.1-588, A.1-595, A.1-602, A.1-609,A.1-625, A.1-632, A.1-639, A.1-646, A.1-653, A.1-660, A.1-667, A.1-674,A.1-681, A.1-688, A.1-695, A.1-702, A.1-709, A.1-716, A.1-723, A.1-730,A.1-737, A.1-744, A.1-751, A.1-758, A.1-765, A.1-772, A.1-779, A.1-786,A.1-793, A.1-809, A.1-816, A.1-823, A.1-830, A.1-837, A.1-844, A.1-851,A.1-858, A.1-865, A.1-872, A.1-879, A.1-886, A.1-893, A.1-900, A.1-907,A.1-914, A.1-921, A.1-928, A.1-935, A.1-942, A.1-949, A.1-956, A.1-963,A.1-970, A.1-977, A.1-993, A.1-1000, A.1-1007, A.1-1014, A.1-1021,A.1-1028, A.1-1035, A.1-1042, A.1-1049, A.1-1056, A.1-1063, A.1-1070,A.1-1077, A.1-1084, A.1-1091, A.1-1098, A.1-1105, A.1-1112, A.1-1119,A.1-1126, A.1-1133, A.1-1140, A.1-1147, A.1-1154, A.1-1161 and A.1-1177only in that R⁵ is F.

Table A.6

Also especially preferred are compounds A.6-7 to A.6-18, A.6-37 toA.6-72, A.6-73, A.6-80, A.6-87, A.6-94, A.6-101, A.6-108, A.6-115,A.6-122, A.6-129, A.6-136, A.6-143, A.6-150, A.6-157, A.6-164, A.6-171,A.6-178, A.6-185, A.6-192, A.6-199, A.6-206, A.6-213, A.6-220, A.6-227,A.6-234, A.6-241, A.6-257, A.6-264, A.6-271, A.6-278, A.6-285, A.6-292,A.6-299, A.6-306, A.6-313, A.6-320, A.6-327, A.6-334, A.6-341, A.6-348,A.6-355, A.6-362, A.6-369, A.6-376, A.6-383, A.6-390, A.6-397, A.6-404,A.6-411, A.6-418, A.6-425, A.6-441, A.6-448, A.6-455, A.6-462, A.6-469,A.6-476, A.6-483, A.6-490, A.6-497, A.6-504, A.6-511, A.6-518, A.6-525,A.6-532, A.6-539, A.6-546, A.6-553, A.6-560, A.6-567, A.6-574, A.6-581,A.6-588, A.6-595, A.6-602, A.6-609, A.6-625, A.6-632, A.6-639, A.6-646,A.6-653, A.6-660, A.6-667, A.6-674, A.6-681, A.6-688, A.6-695, A.6-702,A.6-709, A.6-716, A.6-723, A.6-730, A.6-737, A.6-744, A.6-751, A.6-758,A.6-765, A.6-772, A.6-779, A.6-786, A.6-793, A.6-809, A.6-816, A.6-823,A.6-830, A.6-837, A.6-844, A.6-851, A.6-858, A.6-865, A.6-872, A.6-879,A.6-886, A.6-893, A.6-900, A.6-907, A.6-914, A.6-921, A.6-928, A.6-935,A.6-942, A.6-949, A.6-956, A.6-963, A.6-970, A.6-977, A.6-993, A.6-1000,A.6-1007, A.6-1014, A.6-1021, A.6-1028, A.6-1035, A.6-1042, A.6-1049,A.6-1056, A.6-1063, A.6-1070, A.6-1077, A.6-1084, A.6-1091, A.6-1098,A.6-1105, A.6-1112, A.6-1119, A.6-1126, A.6-1133, A.6-1140, A.6-1147,A.6-1154, A.6-1161 and A.6-1177 which differ from the correspondingcompounds A.1-7 to A.1-18, A.1-37 to A.1-72, A.1-73, A.1-80, A.1-87,A.1-94, A.1-101, A.1-108, A.1-115, A.1-122, A.1-129, A.1-136, A.1-143,A.1-150, A.1-157, A.1-164, A.1-171, A.1-178, A.1-185, A.1-192, A.1-199,A.1-206, A.1-213, A.1-220, A.1-227, A.1-234, A.1-241, A.1-257, A.1-264,A.1-271, A.1-278, A.1-285, A.1-292, A.1-299, A.1-306, A.1-313, A.1-320,A.1-327, A.1-334, A.1-341, A.1-348, A.1-355, A.1-362, A.1-369, A.1-376,A.1-383, A.1-390, A.1-397, A.1-404, A.1-411, A.1-418, A.1-425, A.1-441,A.1-448, A.1-455, A.1-462, A.1-469, A.1-476, A.1-483, A.1-490, A.1-497,A.1-504, A.1-511, A.1-518, A.1-525, A.1-532, A.1-539, A.1-546, A.1-553,A.1-560, A.1-567, A.1-574, A.1-581, A.1-588, A.1-595, A.1-602, A.1-609,A.1-625, A.1-632, A.1-639, A.1-646, A.1-653, A.1-660, A.1-667, A.1-674,A.1-681, A.1-688, A.1-695, A.1-702, A.1-709, A.1-716, A.1-723, A.1-730,A.1-737, A.1-744, A.1-751, A.1-758, A.1-765, A.1-772, A.1-779, A.1-786,A.1-793, A.1-809, A.1-816, A.1-823, A.1-830, A.1-837, A.1-844, A.1-851,A.1-858, A.1-865, A.1-872, A.1-879, A.1-886, A.1-893, A.1-900, A.1-907,A.1-914, A.1-921, A.1-928, A.1-935, A.1-942, A.1-949, A.1-956, A.1-963,A.1-970, A.1-977, A.1-993, A.1-1000, A.1-1007, A.1-1014, A.1-1021,A.1-1028, A.1-1035, A.1-1042, A.1-1049, A.1-1056, A.1-1063, A.1-1070,A.1-1077, A.1-1084, A.1-1091, A.1-1098, A.1-1105, A.1-1112, A.1-1119,A.1-1126, A.1-1133, A.1-1140, A.1-1147, A.1-1154, A.1-1161 and A.1-1177only in that R⁵ is Cl.

Table A.7

Also especially preferred are compounds A.7-7 to A.7-18, A.7-37 toA.7-72, A.7-73, A.7-80, A.7-87, A.7-94, A.7-101, A.7-108, A.7-115,A.7-122, A.7-129, A.7-136, A.7-143, A.7-150, A.7-157, A.7-164, A.7-171,A.7-178, A.7-185, A.7-192, A.7-199, A.7-206, A.7-213, A.7-220, A.7-227,A.7-234, A.7-241, A.7-257, A.7-264, A.7-271, A.7-278, A.7-285, A.7-292,A.7-299, A.7-306, A.7-313, A.7-320, A.7-327, A.7-334, A.7-341, A.7-348,A.7-355, A.7-362, A.7-369, A.7-376, A.7-383, A.7-390, A.7-397, A.7-404,A.7-411, A.7-418, A.7-425, A.7-441, A.7-448, A.7-455, A.7-462, A.7-469,A.7-476, A.7-483, A.7-490, A.7-497, A.7-504, A.7-511, A.7-518, A.7-525,A.7-532, A.7-539, A.7-546, A.7-553, A.7-560, A.7-567, A.7-574, A.7-581,A.7-588, A.7-595, A.7-602, A.7-609, A.7-625, A.7-632, A.7-639, A.7-646,A.7-653, A.7-660, A.7-667, A.7-674, A.7-681, A.7-688, A.7-695, A.7-702,A.7-709, A.7-716, A.7-723, A.7-730, A.7-737, A.7-744, A.7-751, A.7-758,A.7-765, A.7-772, A.7-779, A.7-786, A.7-793, A.7-809, A.7-816, A.7-823,A.7-830, A.7-837, A.7-844, A.7-851, A.7-858, A.7-865, A.7-872, A.7-879,A.7-886, A.7-893, A.7-900, A.7-907, A.7-914, A.7-921, A.7-928, A.7-935,A.7-942, A.7-949, A.7-956, A.7-963, A.7-970, A.7-977, A.7-993, A.7-1000,A.7-1007, A.7-1014, A.7-1021, A.7-1028, A.7-1035, A.7-1042, A.7-1049,A.7-1056, A.7-1063, A.7-1070, A.7-1077, A.7-1084, A.7-1091, A.7-1098,A.7-1105, A.7-1112, A.7-1119, A.7-1126, A.7-1133, A.7-1140, A.7-1147,A.7-1154, A.7-1161 and A.7-1177 which differ from the correspondingcompounds A.2-7 to A.2-18, A.2-37 to A.2-72, A.2-73, A.2-80, A.2-87,A.2-94, A.2-101, A.2-108, A.2-115, A.2-122, A.2-129, A.2-136, A.2-143,A.2-150, A.2-157, A.2-164, A.2-171, A.2-178, A.2-185, A.2-192, A.2-199,A.2-206, A.2-213, A.2-220, A.2-227, A.2-234, A.2-241, A.2-257, A.2-264,A.2-271, A.2-278, A.2-285, A.2-292, A.2-299, A.2-306, A.2-313, A.2-320,A.2-327, A.2-334, A.2-341, A.2-348, A.2-355, A.2-362, A.2-369, A.2-376,A.2-383, A.2-390, A.2-397, A.2-404, A.2-411, A.2-418, A.2-425, A.2-441,A.2-448, A.2-455, A.2-462, A.2-469, A.2-476, A.2-483, A.2-490, A.2-497,A.2-504, A.2-511, A.2-518, A.2-525, A.2-532, A.2-539, A.2-546, A.2-553,A.2-560, A.2-567, A.2-574, A.2-581, A.2-588, A.2-595, A.2-602, A.2-609,A.2-625, A.2-632, A.2-639, A.2-646, A.2-653, A.2-660, A.2-667, A.2-674,A.2-681, A.2-688, A.2-695, A.2-702, A.2-709, A.2-716, A.2-723, A.2-730,A.2-737, A.2-744, A.2-751, A.2-758, A.2-765, A.2-772, A.2-779, A.2-786,A.2-793, A.2-809, A.2-816, A.2-823, A.2-830, A.2-837, A.2-844, A.2-851,A.2-858, A.2-865, A.2-872, A.2-879, A.2-886, A.2-893, A.2-900, A.2-907,A.2-914, A.2-921, A.2-928, A.2-935, A.2-942, A.2-949, A.2-956, A.2-963,A.2-970, A.2-977, A.2-993, A.2-1000, A.2-1007, A.2-1014, A.2-1021,A.2-1028, A.2-1035, A.2-1042, A.2-1049, A.2-1056, A.2-1063, A.2-1070,A.2-1077, A.2-1084, A.2-1091, A.2-1098, A.2-1105, A.2-1112, A.2-1119,A.2-1126, A.2-1133, A.2-1140, A.2-1147, A.2-1154, A.2-1161 and A.2-1177only in that R⁵ is F.

Table A.8

Also especially preferred are compounds A.8-7 to A.8-18, A.8-37 toA.8-72, A.8-73, A.8-80, A.8-87, A.8-94, A.8-101, A.8-108, A.8-115,A.8-122, A.8-129, A.8-136, A.8-143, A.8-150, A.8-157, A.8-164, A.8-171,A.8-178, A.8-185, A.8-192, A.8-199, A.8-206, A.8-213, A.8-220, A.8-227,A.8-234, A.8-241, A.8-257, A.8-264, A.8-271, A.8-278, A.8-285, A.8-292,A.8-299, A.8-306, A.8-313, A.8-320, A.8-327, A.8-334, A.8-341, A.8-348,A.8-355, A.8-362, A.8-369, A.8-376, A.8-383, A.8-390, A.8-397, A.8-404,A.8-411, A.8-418, A.8-425, A.8-441, A.8-448, A.8-455, A.8-462, A.8-469,A.8-476, A.8-483, A.8-490, A.8-497, A.8-504, A.8-511, A.8-518, A.8-525,A.8-532, A.8-539, A.8-546, A.8-553, A.8-560, A.8-567, A.8-574, A.8-581,A.8-588, A.8-595, A.8-602, A.8-609, A.8-625, A.8-632, A.8-639, A.8-646,A.8-653, A.8-660, A.8-667, A.8-674, A.8-681, A.8-688, A.8-695, A.8-702,A.8-709, A.8-716, A.8-723, A.8-730, A.8-737, A.8-744, A.8-751, A.8-758,A.8-765, A.8-772, A.8-779, A.8-786, A.8-793, A.8-809, A.8-816, A.8-823,A.8-830, A.8-837, A.8-844, A.8-851, A.8-858, A.8-865, A.8-872, A.8-879,A.8-886, A.8-893, A.8-900, A.8-907, A.8-914, A.8-921, A.8-928, A.8-935,A.8-942, A.8-949, A.8-956, A.8-963, A.8-970, A.8-977, A.8-993, A.8-1000,A.8-1007, A.8-1014, A.8-1021, A.8-1028, A.8-1035, A.8-1042, A.8-1049,A.8-1056, A.8-1063, A.8-1070, A.8-1077, A.8-1084, A.8-1091, A.8-1098,A.8-1105, A.8-1112, A.8-1119, A.8-1126, A.8-1133, A.8-1140, A.8-1147,A.8-1154, A.8-1161 and A.8-1177 which differ from the correspondingcompounds A.2-7 to A.2-18, A.2-37 to A.2-72, A.2-73, A.2-80, A.2-87,A.2-94, A.2-101, A.2-108, A.2-115, A.2-122, A.2-129, A.2-136, A.2-143,A.2-150, A.2-157, A.2-164, A.2-171, A.2-178, A.2-185, A.2-192, A.2-199,A.2-206, A.2-213, A.2-220, A.2-227, A.2-234, A.2-241, A.2-257, A.2-264,A.2-271, A.2-278, A.2-285, A.2-292, A.2-299, A.2-306, A.2-313, A.2-320,A.2-327, A.2-334, A.2-341, A.2-348, A.2-355, A.2-362, A.2-369, A.2-376,A.2-383, A.2-390, A.2-397, A.2-404, A.2-411, A.2-418, A.2-425, A.2-441,A.2-448, A.2-455, A.2-462, A.2-469, A.2-476, A.2-483, A.2-490, A.2-497,A.2-504, A.2-511, A.2-518, A.2-525, A.2-532, A.2-539, A.2-546, A.2-553,A.2-560, A.2-567, A.2-574, A.2-581, A.2-588, A.2-595, A.2-602, A.2-609,A.2-625, A.2-632, A.2-639, A.2-646, A.2-653, A.2-660, A.2-667, A.2-674,A.2-681, A.2-688, A.2-695, A.2-702, A.2-709, A.2-716, A.2-723, A.2-730,A.2-737, A.2-744, A.2-751, A.2-758, A.2-765, A.2-772, A.2-779, A.2-786,A.2-793, A.2-809, A.2-816, A.2-823, A.2-830, A.2-837, A.2-844, A.2-851,A.2-858, A.2-865, A.2-872, A.2-879, A.2-886, A.2-893, A.2-900, A.2-907,A.2-914, A.2-921, A.2-928, A.2-935, A.2-942, A.2-949, A.2-956, A.2-963,A.2-970, A.2-977, A.2-993, A.2-1000, A.2-1007, A.2-1014, A.2-1021,A.2-1028, A.2-1035, A.2-1042, A.2-1049, A.2-1056, A.2-1063, A.2-1070,A.2-1077, A.2-1084, A.2-1091, A.2-1098, A.2-1105, A.2-1112, A.2-1119,A.2-1126, A.2-1133, A.2-1140, A.2-1147, A.2-1154, A.2-1161 and A.2-1177only in that R⁵ is Cl.

The compounds I and their agriculturally useful salts are suitable, bothas isomer mixtures and in the form of the pure isomers, as herbicides.They are suitable as such or as an appropriately formulated composition.The herbicidal compositions comprising the compound I, in particular thepreferred aspects thereof, control vegetation on non-crop areas veryefficiently, especially at high rates of application. They act againstbroad-leaved weeds and weed grasses in crops such as wheat, rice, corn,soybeans and cotton without causing any significant damage to the cropplants. This effect is mainly observed at low rates of application.

Depending on the application method in question, the compounds I, inparticular the preferred aspects thereof, or compositions comprisingthem can additionally be employed in a further number of crop plants foreliminating unwanted plants. Examples of suitable crops are thefollowing:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa,Brassica napus var. napus, Brassica napus var. napobrassica, Brassicarapa var. silvestris, Brassica oleracea, Brassica nigra, Camelliasinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon,Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica),Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis,Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum,Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Heveabrasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglansregia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum,Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotianatabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus,Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisumsativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca,Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre,Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba,Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao,Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Viciafaba, Vitis vinifera, Zea mays.

The term “crop plants” also includes plants which have been modified bybreeding, mutagenesis or genetic engineering. Genetically modifiedplants are plants whose genetic material has been modified in a mannerwhich does not occur under natural conditions by crossing, mutations ornatural recombination (i.e. reassembly of the genetic information).Here, in general, one or more genes are integrated into the geneticmaterial of the plant to improve the properties of the plant.

Accordingly, the term “crop plants” also includes plants which, bybreeding and genetic engineering, have acquired tolerance to certainclasses of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD)inhibitors, acetolactate synthase (ALS) inhibitors, such as, forexample, sulfonylureas (EP-A-0257993, U.S. Pat. No. 5,013,659) orimidazolinones (see, for example, U.S. Pat. No. 6,222,100, WO 01/82685,WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073),enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors, such as,for example, glyphosate (see, for example, WO 92/00377), glutaminesynthetase (GS) inhibitors, such as, for example, glufosinate (see, forexample, EP-A-0242236, EP-A-242246), or oxynil herbicides (see, forexample, U.S. Pat. No. 5,559,024).

Numerous crop plants, for example Clearfield® oilseed rape, tolerant toimidazolinones, for example imazamox, have been generated with the aidof classic breeding methods (mutagenesis). Crop plants such as soybeans,cotton, corn, beet and oilseed rape, resistant to glyphosate orglufosinate, which are available under the tradenames RoundupReady®(glyphosate) and Liberty Link® (glufosinate) have been generated withthe aid of genetic engineering methods.

Accordingly, the term “crop plants” also includes plants which, with theaid of genetic engineering, produce one or more toxins, for examplethose of the bacterial strain Bacillus ssp. Toxins which are produced bysuch genetically modified plants include, for example, insecticidalproteins of Bacillus spp., in particular B. thuringiensis, such as theendotoxins Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1,Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs),for example VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins ofnematode-colonizing bacteria, for example Photorhabdus spp. orXenorhabdus spp.; toxins of animal organisms, for example wasp, spideror scorpion toxins; fungal toxins, for example from Streptomycetes;plant lectins, for example from peas or barley; agglutinins; proteinaseinhibitors, for example trypsin inhibitors, serine protease inhibitors,patatin, cystatin or papain inhibitors, ribosome-inactivating proteins(RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin;steroid-metabolizing enzymes, for example 3-hydroxy-steroid oxidase,ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdysoneinhibitors, or HMG-CoA reductase; ion channel blockers, for exampleinhibitors of sodium channels or calcium channels; juvenile hormoneesterase; receptors of the diuretic hormone (helicokinin receptors);stilbene synthase, bibenzyl synthase, chitinases and glucanases. In theplants, these toxins may also be produced as pretoxins, hybrid proteinsor truncated or otherwise modified proteins. Hybrid proteins arecharacterized by a novel combination of different protein domains (see,for example, WO 2002/015701). Further examples of such toxins orgenetically modified plants which produce these toxins are disclosed inEP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO03/018810 and WO 03/052073. The methods for producing these geneticallymodified plants are known to the person skilled in the art anddisclosed, for example, in the publications mentioned above. Numerous ofthe toxins mentioned above bestow, upon the plants by which they areproduced, tolerance to pests from all taxonomic classes of arthropods,in particular to beetles (Coeleropta), dipterans (Diptera) andbutterflies (Lepidoptera) and to nematodes (Nematoda).

Genetically modified plants which produce one or more genes coding forinsecticidal toxins are described, for example, in the publicationsmentioned above, and some of them are commercially available, such as,for example, YieldGard® (corn varieties producing the toxin Cry1Ab),YieldGard® Plus (corn varieties which produce the toxins Cry1Ab andCry3Bb1), Starlink® (corn varieties which produce the toxin Cry9c),Herculex® RW (corn varieties which produce the toxins Cry34Ab1, Cry35Ab1and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B(cotton varieties which produce the toxin Cry1Ac), Bollgard® I (cottonvarieties which produce the toxin Cry1Ac), Bollgard® II (cottonvarieties which produce the toxins Cry1Ac and Cry2Ab2); VIPCOT® (cottonvarieties which produce a VIP toxin); NewLeaf® (potato varieties whichproduce the toxin Cry3A); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®,Protecta®, Bt11 (for example Agrisure® CB) and Bt176 from Syngenta SeedsSAS, France (corn varieties which produce the toxin Cry1Ab and the PATenyzme), MIR604 from Syngenta Seeds SAS, France (corn varieties whichproduce a modified version of the toxin Cry3A, see WO 03/018810), MON863 from Monsanto Europe S.A., Belgium (corn varieties which produce thetoxin Cry3Bb1), IPC 531 from Monsanto Europe S.A., Belgium (cottonvarieties which produce a modified version of the toxin Cry1Ac) and 1507from Pioneer Overseas Corporation, Belgium (corn varieties which producethe toxin Cry1F and the PAT enzyme).

Accordingly, the term “crop plants” also includes plants which, with theaid of genetic engineering, produce one or more proteins which are morerobust or have increased resistance to bacterial, viral or fungalpathogens, such as, for example, pathogenesis-related proteins (PRproteins, see EP-A 0 392 225), resistance proteins (for example potatovarieties producing two resistance genes against Phytophthora infestansfrom the wild Mexican potato Solanum bulbocastanum) or T4 lysozyme (forexample potato cultivars which, by producing this protein, are resistantto bacteria such as Erwinia amylvora).

Accordingly, the term “crop plants” also includes plants whoseproductivity has been improved with the aid of genetic engineeringmethods, for example by enhancing the potential yield (for examplebiomass, grain yield, starch, oil or protein content), tolerance todrought, salt or other limiting environmental factors or resistance topests and fungal, bacterial and viral pathogens.

The term “crop plants” also includes plants whose ingredients have beenmodified with the aid of genetic engineering methods in particular forimproving human or animal diet, for example by oil plants producinghealth-promoting long-chain omega 3 fatty acids or monounsaturated omega9 fatty acids (for example Nexera® oilseed rape).

The term “crop plants” also includes plants which have been modifiedwith the aid of genetic engineering methods for improving the productionof raw materials, for example by increasing the amylopectin content ofpotatoes (Amflora® potato).

Furthermore, it has been found that the compounds of the formula I arealso suitable for the defoliation and/or desiccation of plant parts, forwhich crop plants such as cotton, potato, oilseed rape, sunflower,soybean or field beans, in particular cotton, are suitable. In thisregard, there have been found compositions for the desiccation and/ordefoliation of plants, processes for preparing these compositions andmethods for desiccating and/or defoliating plants using the compounds ofthe formula I.

As desiccants, the compounds of the formula I are particularly suitablefor desiccating the above-ground parts of crop plants such as potato,oilseed rape, sunflower and soybean, but also cereals. This makespossible the fully mechanical harvesting of these important crop plants.

Also of economic interest is to facilitate harvesting, which is madepossible by concentrating within a certain period of time thedehiscence, or reduction of adhesion to the tree, in citrus fruit,olives and other species and varieties of pomaceous fruit, stone fruitand nuts. The same mechanism, i.e. the promotion of the development ofabscission tissue between fruit part or leaf part and shoot part of theplants is also essential for the readily controllable defoliation ofuseful plants, in particular cotton.

Moreover, a shortening of the time interval in which the individualcotton plants mature leads to an increased fiber quality afterharvesting.

The compounds I, or the herbicidal compositions comprising the compoundsI, can be used, for example, in the form of ready-to-spray aqueoussolutions, powders, suspensions, also highly concentrated aqueous, oilyor other suspensions or dispersions, emulsions, oil dispersions, pastes,dusts, materials for broadcasting, or granules, by means of spraying,atomizing, dusting, spreading, watering or treatment of the seed ormixing with the seed. The use forms depend on the intended purpose; ineach case, they should ensure the finest possible distribution of theactive ingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount ofat least one compound of the formula I or an agriculturally useful saltof I, and auxiliaries which are customary for the formulation of cropprotection agents.

Examples of auxiliaries customary for the formulation of crop protectionagents are inert auxiliaries, solid carriers, surfactants (such asdispersants, protective colloids, emulsifiers, wetting agents andtackifiers), organic and inorganic thickeners, bactericides, antifreezeagents, antifoams, if appropriate colorants and, for seed formulations,adhesives.

Examples of thickeners (i.e. compounds which impart to the formulationmodified flow properties, i.e. high viscosity in the state of rest andlow viscosity in motion) are polysaccharides, such as xanthan gum(Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T.Vanderbilt), and also organic and inorganic sheet minerals, such asAttaclay® (from Engelhardt).

Examples of antifoams are silicone emulsions (such as, for example,Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols,fatty acids, salts of fatty acids, organofluorine compounds and mixturesthereof.

Bactericides can be added for stabilizing the aqueous herbicidalformulation. Examples of bactericides are bactericides based ondichlorophen and benzyl alcohol hemiformal (Proxel® from ICI orActicide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and alsoisothiazolinone derivates, such as alkylisothiazolinones andbenzisothiazolinones (Acticide MBS from Thor Chemie).

Examples of antifreeze agents are ethylene glycol, propylene glycol,urea or glycerol.

Examples of colorants are both sparingly water-soluble pigments andwater-soluble dyes. Examples which may be mentioned are the dyes knownunder the names Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1,and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2,pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13,pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1,pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25,basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14,acid blue 9, acid yellow 23, basic red 10, basic red 108.

Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate,polyvinyl alcohol and tylose.

Suitable inert auxiliaries are, for example, the following:

mineral oil fractions of medium to high boiling point, such as keroseneand diesel oil, furthermore coal tar oils and oils of vegetable oranimal origin, aliphatic, cyclic and aromatic hydrocarbons, for exampleparaffin, tetrahydronaphthalene, alkylated naphthalenes and theirderivatives, alkylated benzenes and their derivatives, alcohols such asmethanol, ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone or strongly polar solvents, for example amines such asN-methylpyrrolidone, and water.

Solid carriers are mineral earths such as silicas, silica gels,silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay,dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate andmagnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersantsand also emulsifiers) are the alkali metal salts, alkaline earth metalsalts and ammonium salts of aromatic sulfonic acids, for examplelignosulfonic acids (e.g. Borrespers-types, Borregaard), phenolsulfonicacids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) anddibutylnaphthalenesulfonic acid (Nekal types, BASF SE), and of fattyacids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ethersulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta-and octadecanols, and also of fatty alcohol glycol ethers, condensatesof sulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene or of the naphthalenesulfonic acids withphenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol/ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, laurylalcohol polyglycol ether acetate, sorbitol esters, lignosulfite wasteliquors and proteins, denatured proteins, polysaccharides (e.g.methylcellulose), hydrophobically modified starches, polyvinyl alcohol(Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types),polyalkoxylates, polyvinylamine (BASF SE, Lupamine types),polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone andcopolymers thereof.

Powders, materials for broadcasting and dusts can be prepared by mixingor grinding the active ingredients together with a solid carrier.

Granules, for example coated granules, impregnated granules andhomogeneous granules, can be prepared by binding the active ingredientsto solid carriers.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thecompounds of the formula I or Ia, either as such or dissolved in an oilor solvent, can be homogenized in water by means of a wetting agent,tackifier, dispersant or emulsifier. Alternatively, it is also possibleto prepare concentrates comprising active substance, wetting agent,tackifier, dispersant or emulsifier and, if desired, solvent or oil,which are suitable for dilution with water.

The concentrations of the compounds of the formula I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise from 0.001 to 98% by weight, preferably 0.01 to95% by weight of at least one active compound. The active compounds areemployed in a purity of from 90% to 100%, preferably 95% to 100%(according to NMR spectrum).

The formulations or ready-to-use preparations may also comprise acids,bases or buffer systems, suitable examples being phosphoric acid orsulfuric acid, or urea or ammonia.

The compounds I of the invention can for example be formulated asfollows:

1. Products for Dilution with Water

A Water-Soluble Concentrates

10 parts by weight of active compound are dissolved in 90 parts byweight of water or a water-soluble solvent. As an alternative, wettersor other adjuvants are added. The active compound dissolves upondilution with water. This gives a formulation with an active compoundcontent of 10% by weight.

B Dispersible Concentrates

20 parts by weight of active compound are dissolved in 70 parts byweight of cyclohexanone with addition of 10 parts by weight of adispersant, for example polyvinylpyrrolidone. Dilution with water givesa dispersion. The active compound content is 20% by weight.

C Emulsifiable Concentrates

15 parts by weight of active compound are dissolved in 75 parts byweight of an organic solvent (e.g. alkylaromatics) with addition ofcalcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case5 parts by weight). Dilution with water gives an emulsion. Theformulation has an active compound content of 15% by weight.

D Emulsions

25 parts by weight of active compound are dissolved in 35 parts byweight of an organic solvent (e.g. alkylaromatics) with addition ofcalcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case5 parts by weight). This mixture is introduced into 30 parts by weightof water by means of an emulsifier (e.g. Ultraturrax) and made into ahomogeneous emulsion. Dilution with water gives an emulsion. Theformulation has an active compound content of 25% by weight.

E Suspensions

In an agitated ball mill, 20 parts by weight of active compound arecomminuted with addition of 10 parts by weight of dispersants andwetters and 70 parts by weight of water or an organic solvent to give afine active compound suspension. Dilution with water gives a stablesuspension of the active compound. The active compound content in theformulation is 20% by weight.

F Water-Dispersible Granules and Water-Soluble Granules

50 parts by weight of active compound are ground finely with addition of50 parts by weight of dispersants and wetters and made intowater-dispersible or water-soluble granules by means of technicalappliances (for example extrusion, spray tower, fluidized bed). Dilutionwith water gives a stable dispersion or solution of the active compound.The formulation has an active compound content of 50% by weight.

G Water-Dispersible Powders and Water-Soluble Powders

75 parts by weight of active compound are ground in a rotor-stator millwith addition of 25 parts by weight of dispersants, wetters and silicagel. Dilution with water gives a stable dispersion or solution of theactive compound. The active compound content of the formulation is 75%by weight.

H Gel Formulations

In a ball mill, 20 parts by weight of active compound, 10 parts byweight of dispersant, 1 part by weight of gelling agent and 70 parts byweight of water or of an organic solvent are ground to give a finesuspension. Dilution with water gives a stable suspension with activecompound content of 20% by weight.

2. Products to be Applied Undiluted

I Dusts

5 parts by weight of active compound are ground finely and mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dusting powder with an active compound content of 5% by weight.

J Granules (GR, FG, GG, MG)

0.5 parts by weight of active compound are ground finely and associatedwith 99.5 parts by weight of carriers. Current methods here areextrusion, spray-drying or the fluidized bed. This gives granules to beapplied undiluted with an active compound content of 0.5% by weight.

K ULV solutions (UL)

10 parts by weight of active compound are dissolved in 90 parts byweight of an organic solvent, for example xylene. This gives a productto be applied undiluted with an active compound content of 10% byweight.

The compounds I or the herbicidal compositions comprising them can beapplied pre- or post-emergence, or together with the seed of a cropplant. It is also possible to apply the herbicidal compositions oractive compounds by applying seed, pretreated with the herbicidalcompositions or active compounds, of a crop plant. If the activecompounds are less well tolerated by certain crop plants, applicationtechniques may be used in which the herbicidal compositions are sprayed,with the aid of the spraying equipment, in such a way that as far aspossible they do not come into contact with the leaves of the sensitivecrop plants, while the active compounds reach the leaves of undesirableplants growing underneath, or the bare soil surface (post-directed,lay-by).

In a further embodiment, the compounds of the formula I or theherbicidal compositions can be applied by treating seed.

The treatment of seed comprises essentially all procedures familiar tothe person skilled in the art (seed dressing, seed coating, seeddusting, seed soaking, seed film coating, seed multilayer coating, seedencrusting, seed dripping and seed pelleting) based on the compounds ofthe formula I according to the invention or the compositions preparedtherefrom. Here, the herbicidal compositions can be applied diluted orundiluted.

The term seed comprises seed of all types, such as, for example, corns,seeds, fruits, tubers, cuttings and similar forms. Here, preferably, theterm seed describes corns and seeds.

The seed used can be seed of the useful plants mentioned above, but alsothe seed of transgenic plants or plants obtained by customary breedingmethods.

The rates of application of active compound are from 0.001 to 3.0,preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending onthe control target, the season, the target plants and the growth stage.To treat the seed, the compounds I are generally employed in amounts offrom 0.001 to 10 kg per 100 kg of seed.

It may also be advantageous to use the compounds of the formula I incombination with safeners. Safeners are chemical compounds which preventor reduce damage to useful plants without substantially affecting theherbicidal action of the compounds of the formula I on unwanted plants.They can be used both before sowing (for example in the treatment ofseed, or on cuttings or seedlings) and before or after the emergence ofthe useful plant. The safeners and the compounds of the formula I can beused simultaneously or in succession. Suitable safeners are, forexample, (quinolin-8-oxy)-acetic acids,1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acids,1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acids,4,5-dihydro-5,5-diaryl-3-isoxazole-carboxylic acids, dichloroacetamides,alpha-oximinophenylacetonitriles, acetophenone oximes,4,6-dihalo-2-phenylpyrimidines,N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1,8-naphthalicanhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acids,phosphorothiolates and O-phenyl N-alkylcarbamates and theiragriculturally useful salts and, provided that they have an acidfunction, their agriculturally useful derivatives, such as amides,esters and thioesters.

To broaden the activity spectrum and to obtain synergistic effects, thecompounds of the formula I can be mixed and jointly applied withnumerous representatives of other herbicidal or growth-regulating groupsof active compounds or with safeners. Suitable mixing partners are, forexample, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoricacid and its derivatives, aminotriazoles, anilides,aryloxy/heteroaryl-oxyalkanoic acids and their derivatives, benzoic acidand its derivatives, benzothiadiazinones,2-(hetaroyl/aroyl)-1,3-cyclohexanediones, heteroaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinoline carboxylic acid and its derivatives, chloroacetanilides,cyclohexenone oxime ether derivates, diazines, dichloropropionic acidand its derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- andheteroaryloxyphenoxypropionic esters, phenylacetic acid and itsderivatives, 2-phenylpropionic acid and its derivatives, pyrazoles,phenylpyrazoles, pyridazines, pyridinecarboxylic acid and itsderivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines,triazinones, triazolinones, triazolecarboxamides, uracils and alsophenylpyrazolines and isoxazolines and their derivatives.

Moreover, it may be useful to apply the compounds I alone or incombination with other herbicides or else also mixed with further cropprotection agents, jointly, for example with compositions forcontrolling pests or phytopathogenic fungi or bacteria. Also of interestis the miscibility with mineral salt solutions which are employed foralleviating nutritional and trace element deficiencies. Other additivessuch as nonphytotoxic oils and oil concentrates may also be added.

Examples of herbicides which can be used in combination with thepyridine compounds of the formula I according to the present inventionare:

b1) from the group of the lipid biosynthesis inhibitors:

alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop,clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop,diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P,fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P,fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P,haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop,quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P,quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim,tralkoxydim, benfuresate, butylate, cycloate, dalapon, dimepiperate,EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb,pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate andvernolate;

b2) from the group of the ALS inhibitors:

amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl,bispyribac, bispyribac-sodium, chlorimuron, chlorimuron-ethyl,chlorsulfuron, cinosulfuron, cloransulam, cloransulam-methyl,cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, florasulam, flucarbazone,flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron,flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron,halosulfuron-methyl, imazamethabenz, imazamethabenz-methyl, imazamox,imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron,iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron,metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron,penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone,propoxycarbazone-sodium, prosulfuron, pyrazosulfuron,pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid,pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium,pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl,sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron,thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl,trifloxysulfuron, triflusulfuron, triflusulfuron-methyl andtritosulfuron;

b3) from the group of the photosynthesis inhibitors:

ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil,bromofenoxim, bromoxynil and its salts and esters, chlorobromuron,chloridazone, chlorotoluron, chloroxuron, cyanazine, desmedipham,desmetryn, dimefuron, dimethametryn, diquat, diquat-dibromide, diuron,fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon,isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron,metobenzuron, metoxuron, metribuzin, monolinuron, neburon, paraquat,paraquat-dichloride, paraquat-dimetilsulfate, pentanochlor,phenmedipham, phenmedipham-ethyl, prometon, prometryn, propanil,propazine, pyridafol, pyridate, siduron, simazine, simetryn,tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn,thidiazuron and trietazine;

b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:

acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone,benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl,chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl,flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen,fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen,halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone,profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil,sulfentrazone, thidiazimin,2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[(isopropyl)-methylsulfamoyl]benzamide(H-1; CAS 372137-35-4),ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate(H-2; CAS 353292-31-6),N-ethyl-3-(2,6-dichloro-4-trifluoro-methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-3; CAS 452098-92-9),N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-4; CAS 915396-43-9),N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyl-phenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-5; CAS 452099-05-7),N-tetrahydro-furfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-6; CAS 45100-03-7),3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione,1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione,2-(2,2,7-Trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dioneand1-Methyl-6-trifluoro-methyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione;

b5) from the group of the bleacher herbicides:

aclonifen, amitrol, beflubutamid, benzobicyclon, benzofenap, clomazone,diflufenican, fluridone, fluorochloridone, flurtamone, isoxaflutole,mesotrione, norflurazon, picolinafen, pyrasulfutole, pyrazolynate,pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone,4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one(H-7; CAS 352010-68-5) and4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (H-8;CAS 180608-33-7);

b6) from the group of the EPSP synthase inhibitors:

glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium(sulfosate);

b7) from the group of the glutamine synthase inhibitors:

bilanaphos (bialaphos), bilanaphos-sodium, glufosinate andglufosinate-ammonium;

b8) from the group of the DHP synthase inhibitors:

asulam;

b9) from the group of the mitose inhibitors:

amiprophos, amiprophos-methyl, benfluralin, butamiphos, butralin,carbetamide, chlorpropham, chlorthal, chlorthal-dimethyl, dinitramine,dithiopyr, ethalfluralin, fluchloralin, oryzalin, pendimethalin,prodiamine, propham, propyzamide, tebutam, thiazopyr and trifluralin;

b10) from the group of the VLCFA inhibitors:

acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor,dimethanamid, dimethenamid-P, diphenamid, fentrazamide, flufenacet,mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide,napropamide, pethoxamid, piperophos, pretilachlor, propachlor,propisochlor, pyroxasulfone (KIH-485) and thenylchlor;

Compounds of the formula 2:

in which the variables have the following meanings:Y is phenyl or 5- or 6-membered heteroaryl as defined at the outset,which radicals may be substituted by one to three groups R^(aa); R²¹;R²²; R²³; R²⁴ are H, halogen or C₁-C₄-alkyl; X is O or NH; N is 0 or 1.

Compounds of the formula 2 have in particular the following meanings:

Y is

where # denotes the bond to the skeleton of the molecule; andR²¹, R²², R²³, R²⁴ are H, Cl, F or CH₃; R²⁵ is halogen, C₁-C₄-alkyl orC₁-C₄-haloalkyl; R²⁶ is C₁-C₄-alkyl; R²⁷ is halogen, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy; R²⁸ is H, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl orC₁-C₄-haloalkoxy; M is 0, 1, 2 or 3; X is oxygen; N is 0 or 1.

Preferred compounds of the formula 2 have the following meanings:

Y is

R²¹ is H; R²², R²³ are F; R²⁴ is H or F; X is oxygen; N is 0 or 1.

Particularly preferred compounds of the formula 2 are:3-[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethane-sulfonyl]-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole(2-1);3-{[5-(2,2-difluoro-ethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]fluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole(2-2);4-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl-methyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-3);4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)fluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-4);4-(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoro-methyl-2H-[1,2,3]triazole(2-5);3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole(2-6);4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)difluoromethyl]-2-methyl-5-trifluoro-methyl-2H-[1,2,3]triazole(2-7);3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole(2-8);4-[difluoro-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)methyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-9);

b11) from the group of the cellulose biosynthesis inhibitors:

chlorthiamid, dichlobenil, flupoxam and isoxaben;

b12) from the group of the decoupler herbicides:

dinoseb, dinoterb and DNOC and its salts;

b13) from the group of the auxin herbicides:

2,4-D and its salts and esters, 2,4-DB and its salts and esters,aminopyralid and its salts such asaminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin,benazolin-ethyl, chloramben and its salts and esters, clomeprop,clopyralid and its salts and esters, dicamba and its salts and esters,dichlorpropand its salts and esters, dichlorprop-P and its salts andesters, fluoroxypyr, fluoroxypyr-butomethyl, fluoroxypyr-meptyl, MCPAand its salts and esters, MCPA-thioethyl, MCPB and its salts and esters,mecopropand its salts and esters, mecoprop-P and its salts and esters,picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6)and its salts and esters, triclopyr and its salts and esters, and5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (H-9; CAS858956-08-8) and its salts and esters;

b14) from the group of the auxin transport inhibitors: diflufenzopyr,diflufenzopyr-sodium, naptalam and naptalam-sodium;

b15) from the group of the other herbicides: bromobutide, chlorflurenol,chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet,difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron,endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl,flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol,flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan,maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide,methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone,pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (H-10; CAS499223-49-3) and its salts and esters.

Examples of preferred safeners C are benoxacor, cloquintocet,cyometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate,fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen,mefenpyr, mephenate, naphthalic anhydride, oxabetrinil,4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (H-11; MON4660, CAS71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine(H-12; R-29148, CAS 52836-31-4).

The active compounds of groups b1) to b15) and the safeners C are knownherbicides and safeners, see, for example, The Compendium of PesticideCommon Names (http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke,R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart,1995. Further herbicidally active compounds are known from WO 96/26202,WO 97/41116, WO 97/41117, WO 97/41118, WO 01/83459 and WO 2008/074991and from W. Krämer et al. (ed.) “Modern Crop Protection Compounds”, Vol.1, Wiley VCH, 2007 and the literature quoted therein.

The invention also relates to compositions in the form of a cropprotection composition formulated as a 1-component compositioncomprising an active compound combination comprising at least onepyridine compound of the formula I and at least one further activecompound, preferably selected from the active compounds of groups b1 tob15, and at least one solid or liquid carrier and/or one or moresurfactants and, if desired, one or more further auxiliaries customaryfor crop protection compositions.

The invention also relates to compositions in the form of a cropprotection composition formulated as a 2-component compositioncomprising a first component comprising at least one pyridine compoundof the formula I, a solid or liquid carrier and/or one or moresurfactants and a second component comprising at least one furtheractive compound selected from the active compounds of groups b1 to b15,a solid or liquid carrier and/or one or more surfactants, whereadditionally both components may also comprise further auxiliariescustomary for crop protection compositions.

In binary compositions comprising at least one compound of the formula Ias component A and at least one herbicide B, the weight ratio of theactive compounds A:B is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1.

In binary compositions comprising at least one compound of the formula Ias component A and at least one safener C, the weight ratio of theactive compounds A:C is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1.

In ternary compositions comprising both at least one compound of theformula I as component A, at least one herbicide B and at least onesafener C, the relative parts by weight of the components A:B aregenerally in the range of from 1:1000 to 1000:1, preferably in the rangeof from 1:500 to 500:1, in particular in the range of from 1:250 to250:1 and particularly preferably in the range of from 1:75 to 75:1; theweight ratio of the components A:C is generally in the range of from1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, inparticular in the range of from 1:250 to 250:1 and particularlypreferably in the range of from 1:75 to 75:1; and the weight ratio ofthe components B:C is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1. Preferably, the weight ratio of the components A+B tothe component C is in the range of from 1:500 to 500:1, in particular inthe range of from 1:250 to 250:1 and particularly preferably in therange of from 1:75 to 75:1.

Examples of particularly preferred compositions according to theinvention comprising in each case one individualized compound of theformula I and one mixing partner or a mixing partner combination aregiven in Table B below.

A further aspect of the invention relates to the compositions B-1 toB-1236 listed in Table B below, where in each case one row of Table Bcorresponds to a herbicidal composition comprising one of the compoundsof the formula I individualized in the above description (component 1)and the further active compound from groups b1) to b15) and/or safener Cstated in each case in the row in question (component 2). The activecompounds in the compositions described are in each case preferablypresent in synergistically effective amounts.

TABLE B Herbicide(s) B Safener C B-1 clodinafop-propargyl — B-2cycloxydim — B-3 cyhalofop-butyl — B-4 fenoxaprop-P-ethyl — B-5pinoxaden — B-6 profoxydim — B-7 tepraloxydim — B-8 tralkoxydim — B-9esprocarb — B-10 prosulfocarb — B-11 thiobencarb — B-12 triallate — B-13bensulfuron-methyl — B-14 bispyribac-sodium — B-15 cyclosulfamuron —B-16 flumetsulam — B-17 flupyrsulfuron-methyl-sodium — B-18foramsulfuron — B-19 imazamox — B-20 imazapic — B-21 imazapyr — B-22imazaquin — B-23 imazethapyr — B-24 imazosulfuron — B-25iodosulfuron-methyl-sodium — B-26 mesosulfuron — B-27 nicosulfuron —B-28 penoxsulam — B-29 propoxycarbazone-sodium — B-30pyrazosulfuron-ethyl — B-31 pyroxsulam — B-32 rimsulfuron — B-33sulfosulfuron — B-34 thiencarbazone-methyl — B-35 tritosulfuron — B-362,4-D and its salts and esters — B-37 aminopyralid and its salts andesters — B-38 clopyralid and its salts and esters — B-39 dicamba and itssalts and esters — B-40 fluroxypyr-meptyl — B-41 quinclorac — B-42quinmerac — B-43 H-9 — B-44 diflufenzopyr — B-45 diflufenzopyr-sodium —B-46 clomazone — B-47 diflufenican — B-48 fluorochloridone — B-49isoxaflutol — B-50 mesotrione — B-51 picolinafen — B-52 sulcotrione —B-53 tefuryltrione — B-54 tembotrione — B-55 topramezone — B-56 H-7 —B-57 atrazine — B-58 diuron — B-59 fluometuron — B-60 hexazinone — B-61isoproturon — B-62 metribuzin — B-63 propanil — B-64 terbuthylazine —B-65 paraquat dichloride — B-66 flumioxazin — B-67 oxyfluorfen — B-68saflufenacil — B-69 sulfentrazone — B-70 H-1 — B-71 H-2 — B-72glyphosate — B-73 glyphosate-isopropylammonium — B-74glyphosate-trimesium (sulfosate) — B-75 glufosinate — B-76glufosinate-ammonium — B-77 pendimethalin — B-78 trifluralin — B-79acetochlor — B-80 cafenstrole — B-81 dimethenamid-P — B-82 fentrazamide— B-83 flufenacet — B-84 mefenacet — B-85 metazachlor — B-86metolachlor-S — B-87 pyroxasulfone — B-88 isoxaben — B-89 dymron — B-90indanofan — B-91 oxaziclomefone — B-92 triaziflam — B-93 chlorotoluron —B-94 atrazine + H-1 — B-95 atrazine + glyphosate — B-96 atrazine +mesotrione — B-97 atrazine + nicosulfuron — B-98 atrazine + tembotrione— B-99 atrazine + topramezone — B-100 clomazone + glyphosate — B-101diflufenican + clodinafop-propargyl — B-102 diflufenican +fenoxaprop-P-ethyl — B-103 diflufenican + flupyrsulfuron-methyl-sodium —B-104 diflufenican + glyphosate — B-105 diflufenican +mesosulfuron-methyl — B-106 diflufenican + pinoxaden — B-107diflufenican + pyroxsulam — B-108 flumetsulam + glyphosate — B-109flumioxazin + glyphosate — B-110 imazapic + glyphosate — B-111imazethapyr + glyphosate — B-112 isoxaflutol + H-1 — B-113 isoxaflutol +glyphosate — B-114 metazachlor + H-1 — B-115 metazachlor + glyphosate —B-116 metazachlor + mesotrione — B-117 metazachlor + nicosulfuron —B-118 metazachlor + terbuthylazine — B-119 metazachlor + topramezone —B-120 metribuzin + glyphosate — B-121 pendimethalin + H-1 — B-122pendimethalin + clodinafop-propargyl — B-123 pendimethalin +fenoxaprop-P-ethyl — B-124 pendimethalin + flupyrsulfuron-methyl-sodium— B-125 pendimethalin + glyphosate — B-126 pendimethalin +mesosulfuron-methyl — B-127 pendimethalin + mesotrione — B-128pendimethalin + nicosulfuron — B-129 pendimethalin + pinoxaden — B-130pendimethalin + pyroxsulam — B-131 pendimethalin + tembotrione — B-132pendimethalin + topramezone — B-133 pyroxasulfone + tembotrione — B-134pyroxasulfone + topramezone — B-135 sulfentrazone + glyphosate — B-136terbuthylazine + H-1 — B-137 terbuthylazine + foramsulfuron — B-138terbuthylazine + glyphosate — B-139 terbuthylazine + mesotrione — B-140terbuthylazine + nicosulfuron — B-141 terbuthylazine + tembotrione —B-142 terbuthylazine + topramezone — B-143 trifluralin + glyphosate —B-144 — benoxacor B-145 — cloquintocet B-146 — cyprosulfamide B-147 —dichlormid B-148 — fenchlorazole B-149 — isoxadifen B-150 — mefenpyrB-151 — H-11 B-152 — H-12 B-153 clodinafop-propargyl benoxacor B-154cycloxydim benoxacor B-155 cyhalofop-butyl benoxacor B-156fenoxaprop-P-ethyl benoxacor B-157 pinoxaden benoxacor B-158 profoxydimbenoxacor B-159 tepraloxydim benoxacor B-160 tralkoxydim benoxacor B-161esprocarb benoxacor B-162 prosulfocarb benoxacor B-163 thiobencarbbenoxacor B-164 triallate benoxacor B-165 bensulfuron-methyl benoxacorB-166 bispyribac-sodium benoxacor B-167 cyclosulfamuron benoxacor B-168flumetsulam benoxacor B-169 flupyrsulfuron-methyl-sodium benoxacor B-170foramsulfuron benoxacor B-171 imazamox benoxacor B-172 imazapicbenoxacor B-173 imazapyr benoxacor B-174 imazaquin benoxacor B-175imazethapyr benoxacor B-176 imazosulfuron benoxacor B-177iodosulfuron-methyl-sodium benoxacor B-178 mesosulfuron benoxacor B-179nicosulfuron benoxacor B-180 penoxsulam benoxacor B-181propoxycarbazone-sodium benoxacor B-182 pyrazosulfuron-ethyl benoxacorB-183 pyroxsulam benoxacor B-184 rimsulfuron benoxacor B-185sulfosulfuron benoxacor B-186 thiencarbazone-methyl benoxacor B-187tritosulfuron benoxacor B-188 2,4-D and its salts and esters benoxacorB-189 aminopyralid and its salts and esters benoxacor B-190 clopyralidand its salts and esters benoxacor B-191 dicamba and its salts andesters benoxacor B-192 fluroxypyr-meptyl benoxacor B-193 quincloracbenoxacor B-194 quinmerac benoxacor B-195 H-9 benoxacor B-196diflufenzopyr benoxacor B-197 diflufenzopyr-sodium benoxacor B-198clomazone benoxacor B-199 diflufenican benoxacor B-200 fluorochloridonebenoxacor B-201 isoxaflutol benoxacor B-202 mesotrione benoxacor B-203picolinafen benoxacor B-204 sulcotrione benoxacor B-205 tefuryltrionebenoxacor B-206 tembotrione benoxacor B-207 topramezone benoxacor B-208H-7 benoxacor B-209 atrazine benoxacor B-210 diuron benoxacor B-211fluometuron benoxacor B-212 hexazinone benoxacor B-213 isoproturonbenoxacor B-214 metribuzin benoxacor B-215 propanil benoxacor B-216terbuthylazine benoxacor B-217 paraquat dichloride benoxacor B-218flumioxazin benoxacor B-219 oxyfluorfen benoxacor B-220 saflufenacilbenoxacor B-221 sulfentrazone benoxacor B-222 H-1 benoxacor B-223 H-2benoxacor B-224 glyphosate benoxacor B-225 glyphosate-isopropylammoniumbenoxacor B-226 glyphosate-trimesium (sulfosate) benoxacor B-227glufosinate benoxacor B-228 glufosinate-ammonium benoxacor B-229pendimethalin benoxacor B-230 trifluralin benoxacor B-231 acetochlorbenoxacor B-232 cafenstrole benoxacor B-233 dimethenamid-P benoxacorB-234 fentrazamide benoxacor B-235 flufenacet benoxacor B-236 mefenacetbenoxacor B-237 metazachlor benoxacor B-238 metolachlor-S benoxacorB-239 pyroxasulfone benoxacor B-240 isoxaben benoxacor B-241 dymronbenoxacor B-242 indanofan benoxacor B-243 oxaziclomefone benoxacor B-244triaziflam benoxacor B-245 atrazine + H-1 benoxacor B-246 atrazine +glyphosate benoxacor B-247 atrazine + mesotrione benoxacor B-248atrazine + nicosulfuron benoxacor B-249 atrazine + tembotrione benoxacorB-250 atrazine + topramezone benoxacor B-251 clomazone + glyphosatebenoxacor B-252 diflufenican + clodinafop-propargyl benoxacor B-253diflufenican + fenoxaprop-P-ethyl benoxacor B-254 diflufenican +flupyrsulfuron-methyl-sodium benoxacor B-255 diflufenican + glyphosatebenoxacor B-256 diflufenican + mesosulfuron-methyl benoxacor B-257diflufenican + pinoxaden benoxacor B-258 diflufenican + pyroxsulambenoxacor B-259 flumetsulam + glyphosate benoxacor B-260 flumioxazin +glyphosate benoxacor B-261 imazapic + glyphosate benoxacor B-262imazethapyr + glyphosate benoxacor B-263 isoxaflutol + H-1 benoxacorB-264 isoxaflutol + glyphosate benoxacor B-265 metazachlor + H-1benoxacor B-266 metazachlor + glyphosate benoxacor B-267 metazachlor +mesotrione benoxacor B-268 metazachlor + nicosulfuron benoxacor B-269metazachlor + terbuthylazine benoxacor B-270 metazachlor + topramezonebenoxacor B-271 metribuzin + glyphosate benoxacor B-272 pendimethalin +H-1 benoxacor B-273 pendimethalin + clodinafop-propargyl benoxacor B-274pendimethalin + fenoxaprop-P-ethyl benoxacor B-275 pendimethalin +flupyrsulfuron-methyl-sodium benoxacor B-276 pendimethalin + glyphosatebenoxacor B-277 pendimethalin + mesosulfuron-methyl benoxacor B-278pendimethalin + mesotrione benoxacor B-279 pendimethalin + nicosulfuronbenoxacor B-280 pendimethalin + pinoxaden benoxacor B-281pendimethalin + pyroxsulam benoxacor B-282 pendimethalin + tembotrionebenoxacor B-283 pendimethalin + topramezone benoxacor B-284pyroxasulfone + tembotrione benoxacor B-285 pyroxasulfone + topramezonebenoxacor B-286 sulfentrazone + glyphosate benoxacor B-287terbuthylazine + H-1 benoxacor B-288 terbuthylazine + foramsulfuronbenoxacor B-289 terbuthylazine + glyphosate benoxacor B-290terbuthylazine + mesotrione benoxacor B-291 terbuthylazine +nicosulfuron benoxacor B-292 terbuthylazine + tembotrione benoxacorB-293 terbuthylazine + topramezone benoxacor B-294 trifluralin +glyphosate benoxacor B-295 clodinafop-propargyl cloquintocet B-296cycloxydim cloquintocet B-297 cyhalofop-butyl cloquintocet B-298fenoxaprop-P-ethyl cloquintocet B-299 pinoxaden cloquintocet B-300profoxydim cloquintocet B-301 tepraloxydim cloquintocet B-302tralkoxydim cloquintocet B-303 esprocarb cloquintocet B-304 prosulfocarbcloquintocet B-305 thiobencarb cloquintocet B-306 triallate cloquintocetB-307 bensulfuron-methyl cloquintocet B-308 bispyribac-sodiumcloquintocet B-309 cyclosulfamuron cloquintocet B-310 flumetsulamcloquintocet B-311 flupyrsulfuron-methyl-sodium cloquintocet B-312foramsulfuron cloquintocet B-313 imazamox cloquintocet B-314 imazapiccloquintocet B-315 imazapyr cloquintocet B-316 imazaquin cloquintocetB-317 imazethapyr cloquintocet B-318 imazosulfuron cloquintocet B-319iodosulfuron-methyl-sodium cloquintocet B-320 mesosulfuron cloquintocetB-321 nicosulfuron cloquintocet B-322 penoxsulam cloquintocet B-323propoxycarbazone-sodium cloquintocet B-324 pyrazosulfuron-ethylcloquintocet B-325 pyroxsulam cloquintocet B-326 rimsulfuroncloquintocet B-327 sulfosulfuron cloquintocet B-328thiencarbazone-methyl cloquintocet B-329 tritosulfuron cloquintocetB-330 2,4-D and its salts and esters cloquintocet B-331 aminopyralid andits salts and esters cloquintocet B-332 clopyralid and its salts andesters cloquintocet B-333 dicamba and its salts and esters cloquintocetB-334 fluroxypyr-meptyl cloquintocet B-335 quinclorac cloquintocet B-336quinmerac cloquintocet B-337 H-9 cloquintocet B-338 diflufenzopyrcloquintocet B-339 diflufenzopyr-sodium cloquintocet B-340 clomazonecloquintocet B-341 diflufenican cloquintocet B-342 fluorochloridonecloquintocet B-343 isoxaflutol cloquintocet B-344 mesotrionecloquintocet B-345 picolinafen cloquintocet B-346 sulcotrionecloquintocet B-347 tefuryltrione cloquintocet B-348 tembotrionecloquintocet B-349 topramezone cloquintocet B-350 H-7 cloquintocet B-351atrazine cloquintocet B-352 diuron cloquintocet B-353 fluometuroncloquintocet B-354 hexazinone cloquintocet B-355 isoproturoncloquintocet B-356 metribuzin cloquintocet B-357 propanil cloquintocetB-358 terbuthylazine cloquintocet B-359 paraquat dichloride cloquintocetB-360 flumioxazin cloquintocet B-361 oxyfluorfen cloquintocet B-362saflufenacil cloquintocet B-363 sulfentrazone cloquintocet B-364 H-1cloquintocet B-365 H-2 cloquintocet B-366 glyphosate cloquintocet B-367glyphosate-isopropylammonium cloquintocet B-368 glyphosate-trimesium(sulfosate) cloquintocet B-369 glufosinate cloquintocet B-370glufosinate-ammonium cloquintocet B-371 pendimethalin cloquintocet B-372trifluralin cloquintocet B-373 acetochlor cloquintocet B-374 cafenstrolecloquintocet B-375 dimethenamid-P cloquintocet B-376 fentrazamidecloquintocet B-377 flufenacet cloquintocet B-378 mefenacet cloquintocetB-379 metazachlor cloquintocet B-380 metolachlor-S cloquintocet B-381pyroxasulfone cloquintocet B-382 isoxaben cloquintocet B-383 dymroncloquintocet B-384 indanofan cloquintocet B-385 oxaziclomefonecloquintocet B-386 triaziflam cloquintocet B-387 atrazine + H-1cloquintocet B-388 atrazine + glyphosate cloquintocet B-389 atrazine +mesotrione cloquintocet B-390 atrazine + nicosulfuron cloquintocet B-391atrazine + tembotrione cloquintocet B-392 atrazine + topramezonecloquintocet B-393 clomazone + glyphosate cloquintocet B-394diflufenican + clodinafop-propargyl cloquintocet B-395 diflufenican +fenoxaprop-p-ethyl cloquintocet B-396 diflufenican +flupyrsulfuron-methyl-sodium cloquintocet B-397 diflufenican +glyphosate cloquintocet B-398 diflufenican + mesosulfuron-methylcloquintocet B-399 diflufenican + pinoxaden cloquintocet B-400diflufenican + pyroxsulam cloquintocet B-401 flumetsulam + glyphosatecloquintocet B-402 flumioxazin + glyphosate cloquintocet B-403imazapic + glyphosate cloquintocet B-404 imazethapyr + glyphosatecloquintocet B-405 isoxaflutol + H-1 cloquintocet B-406 isoxaflutol +glyphosate cloquintocet B-407 metazachlor + H-1 cloquintocet B-408metazachlor + glyphosate cloquintocet B-409 metazachlor + mesotrionecloquintocet B-410 metazachlor + nicosulfuron cloquintocet B-411metazachlor + terbuthylazine cloquintocet B-412 metazachlor +topramezone cloquintocet B-413 metribuzin + glyphosate cloquintocetB-414 pendimethalin + H-1 cloquintocet B-415 pendimethalin +clodinafop-propargyl cloquintocet B-416 pendimethalin +fenoxaprop-P-ethyl cloquintocet B-417 pendimethalin +flupyrsulfuron-methyl-sodium cloquintocet B-418 pendimethalin +glyphosate cloquintocet B-419 pendimethalin + mesosulfuron-methylcloquintocet B-420 pendimethalin + mesotrione cloquintocet B-421pendimethalin + nicosulfuron cloquintocet B-422 pendimethalin +pinoxaden cloquintocet B-423 pendimethalin + pyroxsulam cloquintocetB-424 pendimethalin + tembotrione cloquintocet B-425 pendimethalin +topramezone cloquintocet B-426 pyroxasulfone + tembotrione cloquintocetB-427 pyroxasulfone + topramezone cloquintocet B-428 sulfentrazone +glyphosate cloquintocet B-429 terbuthylazine + H-1 cloquintocet B-430terbuthylazine + foramsulfuron cloquintocet B-431 terbuthylazine +glyphosate cloquintocet B-432 terbuthylazine + mesotrione cloquintocetB-433 terbuthylazine + nicosulfuron cloquintocet B-434 terbuthylazine +tembotrione cloquintocet B-435 terbuthylazine + topramezone cloquintocetB-436 trifluralin + glyphosate cloquintocet B-437 clodinafop-propargyldichlormid B-438 cycloxydim dichlormid B-439 cyhalofop-butyl dichlormidB-440 fenoxaprop-P-ethyl dichlormid B-441 pinoxaden dichlormid B-442profoxydim dichlormid B-443 tepraloxydim dichlormid B-444 tralkoxydimdichlormid B-445 esprocarb dichlormid B-446 prosulfocarb dichlormidB-447 thiobencarb dichlormid B-448 triallate dichlormid B-449bensulfuron-methyl dichlormid B-450 bispyribac-sodium dichlormid B-451cyclosulfamuron dichlormid B-452 flumetsulam dichlormid B-453flupyrsulfuron-methyl-sodium dichlormid B-454 foramsulfuron dichlormidB-455 imazamox dichlormid B-456 imazapic dichlormid B-457 imazapyrdichlormid B-458 imazaquin dichlormid B-459 imazethapyr dichlormid B-460imazosulfuron dichlormid B-461 iodosulfuron-methyl-sodium dichlormidB-462 mesosulfuron dichlormid B-463 nicosulfuron dichlormid B-464penoxsulam dichlormid B-465 propoxycarbazone-sodium dichlormid B-466pyrazosulfuron-ethyl dichlormid B-467 pyroxsulam dichlormid B-468rimsulfuron dichlormid B-469 sulfosulfuron dichlormid B-470thiencarbazone-methyl dichlormid B-471 tritosulfuron dichlormid B-4722,4-D and its salts and esters dichlormid B-473 aminopyralid and itssalts and esters dichlormid B-474 clopyralid and its salts and estersdichlormid B-475 dicamba and its salts and esters dichlormid B-476fluroxypyr-meptyl dichlormid B-477 quinclorac dichlormid B-478 quinmeracdichlormid B-479 H-9 dichlormid B-480 diflufenzopyr dichlormid B-481diflufenzopyr-sodium dichlormid B-482 clomazone dichlormid B-483diflufenican dichlormid B-484 fluorochloridone dichlormid B-485isoxaflutol dichlormid B-486 mesotrione dichlormid B-487 picolinafendichlormid B-488 sulcotrione dichlormid B-489 tefuryltrione dichlormidB-490 tembotrione dichlormid B-491 topramezone dichlormid B-492 H-7dichlormid B-493 atrazine dichlormid B-494 diuron dichlormid B-495fluometuron dichlormid B-496 hexazinone dichlormid B-497 isoproturondichlormid B-498 metribuzin dichlormid B-499 propanil dichlormid B-500terbuthylazine dichlormid B-501 paraquat dichloride dichlormid B-502flumioxazin dichlormid B-503 oxyfluorfen dichlormid B-504 saflufenacildichlormid B-505 sulfentrazone dichlormid B-506 H-1 dichlormid B-507 H-2dichlormid B-508 glyphosate dichlormid B-509glyphosate-isopropylammonium dichlormid B-510 glyphosate-trimesium(sulfosate) dichlormid B-511 glufosinate dichlormid B-512glufosinate-ammonium dichlormid B-513 pendimethalin dichlormid B-514trifluralin dichlormid B-515 acetochlor dichlormid B-516 cafenstroledichlormid B-517 dimethenamid-P dichlormid B-518 fentrazamide dichlormidB-519 flufenacet dichlormid B-520 mefenacet dichlormid B-521 metazachlordichlormid B-522 metolachlor-S dichlormid B-523 pyroxasulfone dichlormidB-524 isoxaben dichlormid B-525 dymron dichlormid B-526 indanofandichlormid B-527 oxaziclomefone dichlormid B-528 triaziflam dichlormidB-529 atrazine + H-1 dichlormid B-530 atrazine + glyphosate dichlormidB-531 atrazine + mesotrione dichlormid B-532 atrazine + nicosulfurondichlormid B-533 atrazine + tembotrione dichlormid B-534 atrazine +topramezone dichlormid B-535 clomazone + glyphosate dichlormid B-536diflufenican + clodinafop-propargyl dichlormid B-537 diflufenican +fenoxaprop-p-ethyl dichlormid B-538 diflufenican +flupyrsulfuron-methyl-sodium dichlormid B-539 diflufenican + glyphosatedichlormid B-540 diflufenican + mesosulfuron-methyl dichlormid B-541diflufenican + pinoxaden dichlormid B-542 diflufenican + pyroxsulamdichlormid B-543 flumetsulam + glyphosate dichlormid B-544 flumioxazin +glyphosate dichlormid B-545 imazapic + glyphosate dichlormid B-546imazethapyr + glyphosate dichlormid B-547 isoxaflutol + H-1 dichlormidB-548 isoxaflutol + glyphosate dichlormid B-549 metazachlor + H-1dichlormid B-550 metazachlor + glyphosate dichlormid B-551 metazachlor +mesotrione dichlormid B-552 metazachlor + nicosulfuron dichlormid B-553metazachlor + terbuthylazine dichlormid B-554 metazachlor + topramezonedichlormid B-555 metribuzin + glyphosate dichlormid B-556pendimethalin + H-1 dichlormid B-557 pendimethalin +clodinafop-propargyl dichlormid B-558 pendimethalin + fenoxaprop-P-ethyldichlormid B-559 pendimethalin + flupyrsulfuron-methyl-sodium dichlormidB-560 pendimethalin + glyphosate dichlormid B-561 pendimethalin +mesosulfuron-methyl dichlormid B-562 pendimethalin + mesotrionedichlormid B-563 pendimethalin + nicosulfuron dichlormid B-564pendimethalin + pinoxaden dichlormid B-565 pendimethalin + pyroxsulamdichlormid B-566 pendimethalin + tembotrione dichlormid B-567pendimethalin + topramezone dichlormid B-568 pyroxasulfone + tembotrionedichlormid B-569 pyroxasulfone + topramezone dichlormid B-570sulfentrazone + glyphosate dichlormid B-571 terbuthylazine + H-1dichlormid B-572 terbuthylazine + foramsulfuron dichlormid B-573terbuthylazine + glyphosate dichlormid B-574 terbuthylazine + mesotrionedichlormid B-575 terbuthylazine + nicosulfuron dichlormid B-576terbuthylazine + tembotrione dichlormid B-577 terbuthylazine +topramezone dichlormid B-578 trifluralin + glyphosate dichlormid B-579clodinafop-propargyl fenchlorazole B-580 cycloxydim fenchlorazole B-581cyhalofop-butyl fenchlorazole B-582 fenoxaprop-P-ethyl fenchlorazoleB-583 pinoxaden fenchlorazole B-584 profoxydim fenchlorazole B-585tepraloxydim fenchlorazole B-586 tralkoxydim fenchlorazole B-587esprocarb fenchlorazole B-588 prosulfocarb fenchlorazole B-589thiobencarb fenchlorazole B-590 triallate fenchlorazole B-591bensulfuron-methyl fenchlorazole B-592 bispyribac-sodium fenchlorazoleB-593 cyclosulfamuron fenchlorazole B-594 flumetsulam fenchlorazoleB-595 flupyrsulfuron-methyl-sodium fenchlorazole B-596 foramsulfuronfenchlorazole B-597 imazamox fenchlorazole B-598 imazapic fenchlorazoleB-599 imazapyr fenchlorazole B-600 imazaquin fenchlorazole B-601imazethapyr fenchlorazole B-602 imazosulfuron fenchlorazole B-603iodosulfuron-methyl-sodium fenchlorazole B-604 mesosulfuronfenchlorazole B-605 nicosulfuron fenchlorazole B-606 penoxsulamfenchlorazole B-607 propoxycarbazone-sodium fenchlorazole B-608pyrazosulfuron-ethyl fenchlorazole B-609 pyroxsulam fenchlorazole B-610rimsulfuron fenchlorazole B-611 sulfosulfuron fenchlorazole B-612thiencarbazone-methyl fenchlorazole B-613 tritosulfuron fenchlorazoleB-614 2,4-D and its salts and esters fenchlorazole B-615 aminopyralidand its salts and esters fenchlorazole B-616 clopyralid and its saltsand esters fenchlorazole B-617 dicamba and its salts and estersfenchlorazole B-618 fluroxypyr-meptyl fenchlorazole B-619 quincloracfenchlorazole B-620 quinmerac fenchlorazole B-621 H-9 fenchlorazoleB-622 diflufenzopyr fenchlorazole B-623 diflufenzopyr-sodiumfenchlorazole B-624 clomazone fenchlorazole B-625 diflufenicanfenchlorazole B-626 fluorochloridone fenchlorazole B-627 isoxaflutolfenchlorazole B-628 mesotrione fenchlorazole B-629 picolinafenfenchlorazole B-630 sulcotrione fenchlorazole B-631 tefuryltrionefenchlorazole B-632 tembotrione fenchlorazole B-633 topramezonefenchlorazole B-634 H-7 fenchlorazole B-635 atrazine fenchlorazole B-636diuron fenchlorazole B-637 fluometuron fenchlorazole B-638 hexazinonefenchlorazole B-639 isoproturon fenchlorazole B-640 metribuzinfenchlorazole B-641 propanil fenchlorazole B-642 terbuthylazinefenchlorazole B-643 paraquat dichloride fenchlorazole B-644 flumioxazinfenchlorazole B-645 oxyfluorfen fenchlorazole B-646 saflufenacilfenchlorazole B-647 sulfentrazone fenchlorazole B-648 H-1 fenchlorazoleB-649 H-2 fenchlorazole B-650 glyphosate fenchlorazole B-651glyphosate-isopropylammonium fenchlorazole B-652 glyphosate-trimesium(sulfosate) fenchlorazole B-653 glufosinate fenchlorazole B-654glufosinate-ammonium fenchlorazole B-655 pendimethalin fenchlorazoleB-656 trifluralin fenchlorazole B-657 acetochlor fenchlorazole B-658cafenstrole fenchlorazole B-659 dimethenamid-P fenchlorazole B-660fentrazamide fenchlorazole B-661 flufenacet fenchlorazole B-662mefenacet fenchlorazole B-663 metazachlor fenchlorazole B-664metolachlor-S fenchlorazole B-665 pyroxasulfone fenchlorazole B-666isoxaben fenchlorazole B-667 dymron fenchlorazole B-668 indanofanfenchlorazole B-669 oxaziclomefone fenchlorazole B-670 triaziflamfenchlorazole B-671 atrazine + H-1 fenchlorazole B-672 atrazine +glyphosate fenchlorazole B-673 atrazine + mesotrione fenchlorazole B-674atrazine + nicosulfuron fenchlorazole B-675 atrazine + tembotrionefenchlorazole B-676 atrazine + topramezone fenchlorazole B-677clomazone + glyphosate fenchlorazole B-678 diflufenican +clodinafop-propargyl fenchlorazole B-679 diflufenican +fenoxaprop-P-ethyl fenchlorazole B-680 diflufenican +flupyrsulfuron-methyl-sodium fenchlorazole B-681 diflufenican +glyphosate fenchlorazole B-682 diflufenican + mesosulfuron-methylfenchlorazole B-683 diflufenican + pinoxaden fenchlorazole B-684diflufenican + pyroxsulam fenchlorazole B-685 flumetsulam + glyphosatefenchlorazole B-686 flumioxazin + glyphosate fenchlorazole B-687imazapic + glyphosate fenchlorazole B-688 imazethapyr + glyphosatefenchlorazole B-689 isoxaflutol + H-1 fenchlorazole B-690 isoxaflutol +glyphosate fenchlorazole B-691 metazachlor + H-1 fenchlorazole B-692metazachlor + glyphosate fenchlorazole B-693 metazachlor + mesotrionefenchlorazole B-694 metazachlor + nicosulfuron fenchlorazole B-695metazachlor + terbuthylazine fenchlorazole B-696 metazachlor +topramezone fenchlorazole B-697 metribuzin + glyphosate fenchlorazoleB-698 pendimethalin + H-1 fenchlorazole B-699 pendimethalin +clodinafop-propargyl fenchlorazole B-700 pendimethalin +fenoxaprop-P-ethyl fenchlorazole B-701 pendimethalin +flupyrsulfuron-methyl-sodium fenchlorazole B-702 pendimethalin +glyphosate fenchlorazole B-703 pendimethalin + mesosulfuron-methylfenchlorazole B-704 pendimethalin + mesotrione fenchlorazole B-705pendimethalin + nicosulfuron fenchlorazole B-706 pendimethalin +pinoxaden fenchlorazole B-707 pendimethalin + pyroxsulam fenchlorazoleB-708 pendimethalin + tembotrione fenchlorazole B-709 pendimethalin +topramezone fenchlorazole B-710 pyroxasulfone + tembotrionefenchlorazole B-711 pyroxasulfone + topramezone fenchlorazole B-712sulfentrazone + glyphosate fenchlorazole B-713 terbuthylazine + H-1fenchlorazole B-714 terbuthylazine + foramsulfuron fenchlorazole B-715terbuthylazine + glyphosate fenchlorazole B-716 terbuthylazine +mesotrione fenchlorazole B-717 terbuthylazine + nicosulfuronfenchlorazole B-718 terbuthylazine + tembotrione fenchlorazole B-719terbuthylazine + topramezone fenchlorazole B-720 trifluralin +glyphosate fenchlorazole B-721 clodinafop-propargyl isoxadifen B-722cycloxydim isoxadifen B-723 cyhalofop-butyl isoxadifen B-724fenoxaprop-P-ethyl isoxadifen B-725 pinoxaden isoxadifen B-726profoxydim isoxadifen B-727 tepraloxydim isoxadifen B-728 tralkoxydimisoxadifen B-729 esprocarb isoxadifen B-730 prosulfocarb isoxadifenB-731 thiobencarb isoxadifen B-732 triallate isoxadifen B-733bensulfuron-methyl isoxadifen B-734 bispyribac-sodium isoxadifen B-735cyclosulfamuron isoxadifen B-736 flumetsulam isoxadifen B-737flupyrsulfuron-methyl-sodium isoxadifen B-738 foramsulfuron isoxadifenB-739 imazamox isoxadifen B-740 imazapic isoxadifen B-741 imazapyrisoxadifen B-742 imazaquin isoxadifen B-743 imazethapyr isoxadifen B-744imazosulfuron isoxadifen B-745 iodosulfuron-methyl-sodium isoxadifenB-746 mesosulfuron isoxadifen B-747 nicosulfuron isoxadifen B-748penoxsulam isoxadifen B-749 propoxycarbazone-sodium isoxadifen B-750pyrazosulfuron-ethyl isoxadifen B-751 pyroxsulam isoxadifen B-752rimsulfuron isoxadifen B-753 sulfosulfuron isoxadifen B-754thiencarbazone-methyl isoxadifen B-755 tritosulfuron isoxadifen B-7562,4-D and its salts and esters isoxadifen B-757 aminopyralid and itssalts and esters isoxadifen B-758 clopyralid and its salts and estersisoxadifen B-759 dicamba and its salts and esters isoxadifen B-760fluroxypyr-meptyl isoxadifen B-761 quinclorac isoxadifen B-762 quinmeracisoxadifen B-763 H-9 isoxadifen B-764 diflufenzopyr isoxadifen B-765diflufenzopyr-sodium isoxadifen B-766 clomazone isoxadifen B-767diflufenican isoxadifen B-768 fluorochloridone isoxadifen B-769isoxaflutol isoxadifen B-770 mesotrione isoxadifen B-771 picolinafenisoxadifen B-772 sulcotrione isoxadifen B-773 tefuryltrione isoxadifenB-774 tembotrione isoxadifen B-775 topramezone isoxadifen B-776 H-7isoxadifen B-777 atrazine isoxadifen B-778 diuron isoxadifen B-779fluometuron isoxadifen B-780 hexazinone isoxadifen B-781 isoproturonisoxadifen B-782 metribuzin isoxadifen B-783 propanil isoxadifen B-784terbuthylazine isoxadifen B-785 paraquat dichloride isoxadifen B-786flumioxazin isoxadifen B-787 oxyfluorfen isoxadifen B-788 saflufenacilisoxadifen B-789 sulfentrazone isoxadifen B-790 H-1 isoxadifen B-791 H-2isoxadifen B-792 glyphosate isoxadifen B-793glyphosate-isopropylammonium isoxadifen B-794 glyphosate-trimesium(sulfosate) isoxadifen B-795 glufosinate isoxadifen B-796glufosinate-ammonium isoxadifen B-797 pendimethalin isoxadifen B-798trifluralin isoxadifen B-799 acetochlor isoxadifen B-800 cafenstroleisoxadifen B-801 dimethenamid-P isoxadifen B-802 fentrazamide isoxadifenB-803 flufenacet isoxadifen B-804 mefenacet isoxadifen B-805 metazachlorisoxadifen B-806 metolachlor-S isoxadifen B-807 pyroxasulfone isoxadifenB-808 isoxaben isoxadifen B-809 dymron isoxadifen B-810 indanofanisoxadifen B-811 oxaziclomefone isoxadifen B-812 triaziflam isoxadifenB-813 atrazine + H-1 isoxadifen B-814 atrazine + glyphosate isoxadifenB-815 atrazine + mesotrione isoxadifen B-816 atrazine + nicosulfuronisoxadifen B-817 atrazine + tembotrione isoxadifen B-818 atrazine +topramezone isoxadifen B-819 clomazone + glyphosate isoxadifen B-820diflufenican + clodinafop-propargyl isoxadifen B-821 diflufenican +fenoxaprop-P-ethyl isoxadifen B-822 diflufenican +flupyrsulfuron-methyl-sodium isoxadifen B-823 diflufenican + glyphosateisoxadifen B-824 diflufenican + mesosulfuron-methyl isoxadifen B-825diflufenican + pinoxaden isoxadifen B-826 diflufenican + pyroxsulamisoxadifen B-827 flumetsulam + glyphosate isoxadifen B-828 flumioxazin +glyphosate isoxadifen B-829 imazapic + glyphosate isoxadifen B-830imazethapyr + glyphosate isoxadifen B-831 isoxaflutol + H-1 isoxadifenB-832 isoxaflutol + glyphosate isoxadifen B-833 metazachlor + H-1isoxadifen B-834 metazachlor + glyphosate isoxadifen B-835 metazachlor +mesotrione isoxadifen B-836 metazachlor + nicosulfuron isoxadifen B-837metazachlor + terbuthylazine isoxadifen B-838 metazachlor + topramezoneisoxadifen B-839 metribuzin + glyphosate isoxadifen B-840pendimethalin + H-1 isoxadifen B-841 pendimethalin +clodinafop-propargyl isoxadifen B-842 pendimethalin + fenoxaprop-P-ethylisoxadifen B-843 pendimethalin + flupyrsulfuron-methyl-sodium isoxadifenB-844 pendimethalin + glyphosate isoxadifen B-845 pendimethalin +mesosulfuron-methyl isoxadifen B-846 pendimethalin + mesotrioneisoxadifen B-847 pendimethalin + nicosulfuron isoxadifen B-848pendimethalin + pinoxaden isoxadifen B-849 pendimethalin + pyroxsulamisoxadifen B-850 pendimethalin + tembotrione isoxadifen B-851pendimethalin + topramezone isoxadifen B-852 pyroxasulfone + tembotrioneisoxadifen B-853 pyroxasulfone + topramezone isoxadifen B-854sulfentrazone + glyphosate isoxadifen B-855 terbuthylazine + H-1isoxadifen B-856 terbuthylazine + foramsulfuron isoxadifen B-857terbuthylazine + glyphosate isoxadifen B-858 terbuthylazine + mesotrioneisoxadifen B-859 terbuthylazine + nicosulfuron isoxadifen B-860terbuthylazine + tembotrione isoxadifen B-861 terbuthylazine +topramezone isoxadifen B-862 trifluralin + glyphosate isoxadifen B-863clodinafop-propargyl mefenpyr B-864 cycloxydim mefenpyr B-865cyhalofop-butyl mefenpyr B-866 fenoxaprop-P-ethyl mefenpyr B-867pinoxaden mefenpyr B-868 profoxydim mefenpyr B-869 tepraloxydim mefenpyrB-870 tralkoxydim mefenpyr B-871 esprocarb mefenpyr B-872 prosulfocarbmefenpyr B-873 thiobencarb mefenpyr B-874 triallate mefenpyr B-875bensulfuron-methyl mefenpyr B-876 bispyribac-sodium mefenpyr B-877cyclosulfamuron mefenpyr B-878 flumetsulam mefenpyr B-879flupyrsulfuron-methyl-sodium mefenpyr B-880 foramsulfuron mefenpyr B-881imazamox mefenpyr B-882 imazapic mefenpyr B-883 imazapyr mefenpyr B-884imazaquin mefenpyr B-885 imazethapyr mefenpyr B-886 imazosulfuronmefenpyr B-887 iodosulfuron-methyl-sodium mefenpyr B-888 mesosulfuronmefenpyr B-889 nicosulfuron mefenpyr B-890 penoxsulam mefenpyr B-891propoxycarbazone-sodium mefenpyr B-892 pyrazosulfuron-ethyl mefenpyrB-893 pyroxsulam mefenpyr B-894 rimsulfuron mefenpyr B-895 sulfosulfuronmefenpyr B-896 thiencarbazone-methyl mefenpyr B-897 tritosulfuronmefenpyr B-898 2,4-D and its salts and esters mefenpyr B-899aminopyralid and its salts and esters mefenpyr B-900 clopyralid and itssalts and esters mefenpyr B-901 dicamba and its salts and estersmefenpyr B-902 fluroxypyr-meptyl mefenpyr B-903 quinclorac mefenpyrB-904 quinmerac mefenpyr B-905 H-9 mefenpyr B-906 diflufenzopyr mefenpyrB-907 diflufenzopyr-sodium mefenpyr B-908 clomazone mefenpyr B-909diflufenican mefenpyr B-910 fluorochloridone mefenpyr B-911 isoxaflutolmefenpyr B-912 mesotrione mefenpyr B-913 picolinafen mefenpyr B-914sulcotrione mefenpyr B-915 tefuryltrione mefenpyr B-916 tembotrionemefenpyr B-917 topramezone mefenpyr B-918 H-7 mefenpyr B-919 atrazinemefenpyr B-920 diuron mefenpyr B-921 fluometuron mefenpyr B-922hexazinone mefenpyr B-923 isoproturon mefenpyr B-924 metribuzin mefenpyrB-925 propanil mefenpyr B-926 terbuthylazine mefenpyr B-927 paraquatdichloride mefenpyr B-928 flumioxazin mefenpyr B-929 oxyfluorfenmefenpyr B-930 saflufenacil mefenpyr B-931 sulfentrazone mefenpyr B-932H-1 mefenpyr B-933 H-2 mefenpyr B-934 glyphosate mefenpyr B-935glyphosate-isopropylammonium mefenpyr B-936 glyphosate-trimesium(sulfosate) mefenpyr B-937 glufosinate mefenpyr B-938glufosinate-ammonium mefenpyr B-939 pendimethalin mefenpyr B-940trifluralin mefenpyr B-941 acetochlor mefenpyr B-942 cafenstrolemefenpyr B-943 dimethenamid-P mefenpyr B-944 fentrazamide mefenpyr B-945flufenacet mefenpyr B-946 mefenacet mefenpyr B-947 metazachlor mefenpyrB-948 metolachlor-S mefenpyr B-949 pyroxasulfone mefenpyr B-950 isoxabenmefenpyr B-951 dymron mefenpyr B-952 indanofan mefenpyr B-953oxaziclomefone mefenpyr B-954 triaziflam mefenpyr B-955 atrazine + H-1mefenpyr B-956 atrazine + glyphosate mefenpyr B-957 atrazine +mesotrione mefenpyr B-958 atrazine + nicosulfuron mefenpyr B-959atrazine + tembotrione mefenpyr B-960 atrazine + topramezone mefenpyrB-961 clomazone + glyphosate mefenpyr B-962 diflufenican +clodinafop-propargyl mefenpyr B-963 diflufenican + fenoxaprop-P-ethylmefenpyr B-964 diflufenican + flupyrsulfuron-methyl-sodium mefenpyrB-965 diflufenican + glyphosate mefenpyr B-966 diflufenican +mesosulfuron-methyl mefenpyr B-967 diflufenican + pinoxaden mefenpyrB-968 diflufenican + pyroxsulam mefenpyr B-969 flumetsulam + glyphosatemefenpyr B-970 flumioxazin + glyphosate mefenpyr B-971 imazapic +glyphosate mefenpyr B-972 imazethapyr + glyphosate mefenpyr B-973isoxaflutol + H-1 mefenpyr B-974 isoxaflutol + glyphosate mefenpyr B-975metazachlor + H-1 mefenpyr B-976 metazachlor + glyphosate mefenpyr B-977metazachlor + mesotrione mefenpyr B-978 metazachlor + nicosulfuronmefenpyr B-979 metazachlor + terbuthylazine mefenpyr B-980 metazachlor +topramezone mefenpyr B-981 metribuzin + glyphosate mefenpyr B-982pendimethalin + H-1 mefenpyr B-983 pendimethalin + clodinafop-propargylmefenpyr B-984 pendimethalin + fenoxaprop-P-ethyl mefenpyr B-985pendimethalin + flupyrsulfuron-methyl-sodium mefenpyr B-986pendimethalin + glyphosate mefenpyr B-987 pendimethalin +mesosulfuron-methyl mefenpyr B-988 pendimethalin + mesotrione mefenpyrB-989 pendimethalin + nicosulfuron mefenpyr B-990 pendimethalin +pinoxaden mefenpyr B-991 pendimethalin + pyroxsulam mefenpyr B-992pendimethalin + tembotrione mefenpyr B-993 pendimethalin + topramezonemefenpyr B-994 pyroxasulfone + tembotrione mefenpyr B-995pyroxasulfone + topramezone mefenpyr B-996 sulfentrazone + glyphosatemefenpyr B-997 terbuthylazine + H-1 mefenpyr B-998 terbuthylazine +foramsulfuron mefenpyr B-999 terbuthylazine + glyphosate mefenpyr B-1000terbuthylazine + mesotrione mefenpyr B-1001 terbuthylazine +nicosulfuron mefenpyr B-1002 terbuthylazine + tembotrione mefenpyrB-1003 terbuthylazine + topramezone mefenpyr B-1004 trifluralin +glyphosate mefenpyr B-1005 clodinafop-propargyl H-12 B-1006 cycloxydimH-12 B-1007 cyhalofop-butyl H-12 B-1008 fenoxaprop-P-ethyl H-12 B-1009pinoxaden H-12 B-1010 profoxydim H-12 B-1011 tepraloxydim H-12 B-1012tralkoxydim H-12 B-1013 esprocarb H-12 B-1014 prosulfocarb H-12 B-1015thiobencarb H-12 B-1016 triallate H-12 B-1017 bensulfuron-methyl H-12B-1018 bispyribac-sodium H-12 B-1019 cyclosulfamuron H-12 B-1020flumetsulam H-12 B-1021 flupyrsulfuron-methyl-sodium H-12 B-1022foramsulfuron H-12 B-1023 imazamox H-12 B-1024 imazapic H-12 B-1025imazapyr H-12 B-1026 imazaquin H-12 B-1027 imazethapyr H-12 B-1028imazosulfuron H-12 B-1029 iodosulfuron-methyl-sodium H-12 B-1030mesosulfuron H-12 B-1031 nicosulfuron H-12 B-1032 penoxsulam H-12 B-1033propoxycarbazone-sodium H-12 B-1034 pyrazosulfuron-ethyl H-12 B-1035pyroxsulam H-12 B-1036 rimsulfuron H-12 B-1037 sulfosulfuron H-12 B-1038thiencarbazone-methyl H-12 B-1039 tritosulfuron H-12 B-1040 2,4-D andits salts and esters H-12 B-1041 aminopyralid and its salts and estersH-12 B-1042 clopyralid and its salts and esters H-12 B-1043 dicamba andits salts and esters H-12 B-1044 fluroxypyr-meptyl H-12 B-1045quinclorac H-12 B-1046 quinmerac H-12 B-1047 B-9 H-12 B-1048diflufenzopyr H-12 B-1049 diflufenzopyr-sodium H-12 B-1050 clomazoneH-12 B-1051 diflufenican H-12 B-1052 fluorochloridone H-12 B-1053isoxaflutol H-12 B-1054 mesotrione H-12 B-1055 picolinafen H-12 B-1056sulcotrione H-12 B-1057 tefuryltrione H-12 B-1058 tembotrione H-12B-1059 topramezone H-12 B-1060 H-7 H-12 B-1061 atrazine H-12 B-1062diuron H-12 B-1063 fluometuron H-12 B-1064 hexazinone H-12 B-1065isoproturon H-12 B-1066 metribuzin H-12 B-1067 propanil H-12 B-1068terbuthylazine H-12 B-1069 paraquat dichloride H-12 B-1070 flumioxazinH-12 B-1071 oxyfluorfen H-12 B-1072 saflufenacil H-12 B-1073sulfentrazone H-12 B-1074 H-1 H-12 B-1075 H-2 H-12 B-1076 glyphosateH-12 B-1077 glyphosate-isopropylammonium H-12 B-1078glyphosate-trimesium (sulfosate) H-12 B-1079 glufosinate H-12 B-1080glufosinate-ammonium H-12 B-1081 pendimethalin H-12 B-1082 trifluralinH-12 B-1083 acetochlor H-12 B-1084 cafenstrole H-12 B-1085dimethenamid-P H-12 B-1086 fentrazamide H-12 B-1087 flufenacet H-12B-1088 mefenacet H-12 B-1089 metazachlor H-12 B-1090 metolachlor-S H-12B-1091 pyroxasulfone H-12 B-1092 isoxaben H-12 B-1093 dymron H-12 B-1094indanofan H-12 B-1095 oxaziclomefone H-12 B-1096 triaziflam H-12 B-1097atrazine + H-1 H-12 B-1098 atrazine + glyphosate H-12 B-1099 atrazine +mesotrione H-12 B-1100 atrazine + nicosulfuron H-12 B-1101 atrazine +tembotrione H-12 B-1102 atrazine + topramezone H-12 B-1103 clomazone +glyphosate H-12 B-1104 diflufenican + clodinafop-propargyl H-12 B-1105diflufenican + fenoxaprop-P-ethyl H-12 B-1106 diflufenican +flupyrsulfuron-methyl-sodium H-12 B-1107 diflufenican + glyphosate H-12B-1108 diflufenican + mesosulfuron-methyl H-12 B-1109 diflufenican +pinoxaden H-12 B-1110 diflufenican + pyroxsulam H-12 B-1111flumetsulam + glyphosate H-12 B-1112 flumioxazin + glyphosate H-12B-1113 imazapic + glyphosate H-12 B-1114 imazethapyr + glyphosate H-12B-1115 isoxaflutol + H-1 H-12 B-1116 isoxaflutol + glyphosate H-12B-1117 metazachlor + H-1 H-12 B-1118 metazachlor + glyphosate H-12B-1119 metazachlor + mesotrione H-12 B-1120 metazachlor + nicosulfuronH-12 B-1121 metazachlor + terbuthylazine H-12 B-1122 metazachlor +topramezone H-12 B-1123 metribuzin + glyphosate H-12 B-1124pendimethalin + H-1 H-12 B-1125 pendimethalin + clodinafop-propargylH-12 B-1126 pendimethalin + fenoxaprop-P-ethyl H-12 B-1127pendimethalin + flupyrsulfuron-methyl-sodium H-12 B-1128 pendimethalin +glyphosate H-12 B-1129 pendimethalin + mesosulfuron-methyl H-12 B-1130pendimethalin + mesotrione H-12 B-1131 pendimethalin + nicosulfuron H-12B-1132 pendimethalin + pinoxaden H-12 B-1133 pendimethalin + pyroxsulamH-12 B-1134 pendimethalin + tembotrione H-12 B-1135 pendimethalin +topramezone H-12 B-1136 pyroxasulfone + tembotrione H-12 B-1137pyroxasulfone + topramezone H-12 B-1138 sulfentrazone + glyphosate H-12B-1139 terbuthylazine + H-1 H-12 B-1140 terbuthylazine + foramsulfuronH-12 B-1141 terbuthylazine + glyphosate H-12 B-1142 terbuthylazine +mesotrione H-12 B-1143 terbuthylazine + nicosulfuron H-12 B-1144terbuthylazine + tembotrione H-12 B-1145 terbuthylazine + topramezoneH-12 B-1146 trifluralin + glyphosate H-12 B-1147 2-1 — B-1148 2-2 —B-1149 2-3 — B-1150 2-4 — B-1151 2-5 — B-1152 2-6 — B-1153 2-7 — B-11542-8 — B-1155 2-9 — B-1156 2-1 benoxacor B-1157 2-2 benoxacor B-1158 2-3benoxacor B-1159 2-4 benoxacor B-1160 2-5 benoxacor B-1161 2-6 benoxacorB-1162 2-7 benoxacor B-1163 2-8 benoxacor B-1164 2-9 benoxacor B-11652-1 cloquintocet B-1166 2-2 cloquintocet B-1167 2-3 cloquintocet B-11682-4 cloquintocet B-1169 2-5 cloquintocet B-1170 2-6 cloquintocet B-11712-7 cloquintocet B-1172 2-8 cloquintocet B-1173 2-9 cloquintocet B-11742-1 cyprosulfamide B-1175 2-2 cyprosulfamide B-1176 2-3 cyprosulfamideB-1177 2-4 cyprosulfamide B-1178 2-5 cyprosulfamide B-1179 2-6cyprosulfamide B-1180 2-7 cyprosulfamide B-1181 2-8 cyprosulfamideB-1182 2-9 cyprosulfamide B-1183 2-1 dichlormid B-1184 2-2 dichlormidB-1185 2-3 dichlormid B-1186 2-4 dichlormid B-1187 2-5 dichlormid B-11882-6 dichlormid B-1189 2-7 dichlormid B-1190 2-8 dichlormid B-1191 2-9dichlormid B-1192 2-1 fenchlorazole B-1193 2-2 fenchlorazole B-1194 2-3fenchlorazole B-1195 2-4 fenchlorazole B-1196 2-5 fenchlorazole B-11972-6 fenchlorazole B-1198 2-7 fenchlorazole B-1199 2-8 fenchlorazoleB-1200 2-9 fenchlorazole B-1201 2-1 isoxadifen B-1202 2-2 isoxadifenB-1203 2-3 isoxadifen B-1204 2-4 isoxadifen B-1205 2-5 isoxadifen B-12062-6 isoxadifen B-1207 2-7 isoxadifen B-1208 2-8 isoxadifen B-1209 2-9isoxadifen B-1210 2-1 mefenpyr B-1211 2-2 mefenpyr B-1212 2-3 mefenpyrB-1213 2-4 mefenpyr B-1214 2-5 mefenpyr B-1215 2-6 mefenpyr B-1216 2-7mefenpyr B-1217 2-8 mefenpyr B-1218 2-9 mefenpyr B-1219 2-1 H-11 B-12202-2 H-11 B-1221 2-3 H-11 B-1222 2-4 H-11 B-1223 2-5 H-11 B-1224 2-6 H-11B-1225 2-7 H-11 B-1226 2-8 H-11 B-1227 2-9 H-11 B-1228 2-1 H-12 B-12292-2 H-12 B-1230 2-3 H-12 B-1231 2-4 H-12 B-1232 2-5 H-12 B-1233 2-6 H-12B-1234 2-7 H-12 B-1235 2-8 H-12 B-1236 2-9 H-12

The compounds I and the compositions according to the invention may alsohave a plant-strengthening action. Accordingly, they are suitable formobilizing the defense system of the plants against attack by unwantedmicroorganisms, such as harmful fungi, but also viruses and bacteria.Plant-strengthening (resistance-inducing) substances are to beunderstood as meaning, in the present context, those substances whichare capable of stimulating the defense system of treated plants in sucha way that, when subsequently inoculated by unwanted microorganisms, thetreated plants display a substantial degree of resistance to thesemicroorganisms.

The compounds I can be employed for protecting plants against attack byunwanted microorganisms within a certain period of time after thetreatment. The period of time within which their protection is effectedgenerally extends from 1 to 28 days, preferably from 1 to 14 days, afterthe treatment of the plants with the compounds I, or, after treatment ofthe seed, for up to 9 months after sowing.

The compounds I and the compositions according to the invention are alsosuitable for increasing the harvest yield.

Moreover, they have reduced toxicity and are tolerated well by theplants. Hereinbelow, the compounds of the formula I are illustrated byway of examples, without limiting the subject matter of the presentinvention to the examples shown.

I. SYNTHESIS EXAMPLES

With appropriate modification of the starting materials, the proceduresgiven in the synthesis examples below were used to obtain furthercompounds I. The compounds obtained in this manner are listed in thetable that follows, together with physical data.

The products shown below were characterized by determination of themelting point, by NMR spectroscopy or by the masses ([m/z]) or retentiontime (RT; [min.]) determined by HPLC-MS spectrometry.

HPLC-MS=high performance liquid chromatography coupled with massspectrometry; HPLC column:

RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50*4.6 mm;mobile phase: acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1%TFA, using a gradient from 5:95 to 100:0 over 5 minutes at 40° C., flowrate 1.8 ml/min.

MS: quadrupole electrospray ionization, 80 V (positive mode).Ac: Acetyl; THF: tetrahydrofurane; DMF: dimethylformamide;TEA:triethylamine; dppf: 1,1′-bis(diphenylphosphino)ferrocen; dba:dibenzylidenacetone; PE: petrol ether; EtOAc: acetic acid ethyl ester;Et₂O: diethyl ether; DCM: dichloromethane; NCS: N-chlorosuccinimide;LiHMDS: lithium-hexamethyldisilazane; AcOH: acetic acid; MeOH: methanol;m-CPBA: m-chloroperbenzoic acid.

Example 1 Preparation of1-(2,2-difluoroethyl)-2,2-dioxo-3-(2-trifluoromethyl-phenyl)-1,2-dihydro-2-thia-1,5-diazanaphthalen-4-ol[Tab. 31, A-4] Step 1: Methyl3-[(2,2-difluoroethyl)(2-trifluoromethylphenylmethanesulfonyl)amino]-pyridine-2-carboxylate

1.08 g (5.0 mmol) of methyl3-(2,2-difluoroethylamino)pyridine-2-carboxylate (cf. WO2009/090401) anda solution of 5.0 mmol of lithium hexamethyl disilazane in THF wereadded to a solution of 1.29 g (5.0 mmol) of(2-trifluoromethylphenyl)methane-sulfonyl chloride in THF. Work-up gave1.3 g of methyl3-[(2,2-difluoroethyl)-(2-trifluoro-methylphenylmethanesulfonyl)amino]pyridine-2-carboxylate,which was reacted further without further purification.

Step 2:1-(2,2-Difluoroethyl)-2,2-dioxo-3-(2-trifluoromethylphenyl)-1,2-dihydro-2-thia-1,5-diazanaphthalen-4-ol

Potassium carbonate was added to a solution of 1.3 g (3.2 mmol) of theester from Step 1 in DMF. Purification by preparative HPLC gave 345 mgof1-(2,2-difluoroethyl)-2,2-dioxo-3-(2-trifluoromethylphenyl)-1,2-dihydro-2-thia-1,5-diazanaphthalen-4-ol.

¹H-NMR (CDCl₃) δ: 8.50 (d); 7.82 (d); 7.6 (m); 6.1 (tt); 4.33 (m); 4.15(m).

MS (ESI): M+H=407.0

Example 2 Preparation of1-(2,2-difluoroethyl)-3-[3-methylsulfonyl-2-(trifluoromethyl)phenyl]-2,2-dioxo-pyrido[3,2-c]thiazin-4-ol(hereinafter also referred to as compound 10 which corresponds tocompound I-148 in the Table I below)

Step 1: To a solution of compound 1 (6.05 g, 25.0 mmol) in DMF (60 ml)was added sodium methylmercaptide (1.66 g, 23.7 mmol) in portions. Theresulting solution was stirred at room temperature for two hours. Themixture was dissolved in CH₂Cl₂, then washed with water and brine. Theorganic phase was dried and concentrated in vacuum to give crudecompound 2 (6.75 g, 100%) as a colorless syrup used directly withoutfurther purification.

¹H NMR: CDCl₃ 400 MHz δ 7.51-7.47 (m, 1H), 7.23 (d, J=4.8 Hz, 2H), 2.47(s, 2H).

Step 2: To a solution of compound 2 (6.75 g, 25.0 mmol) intoluene/methanol (450 ml/150 ml) was added TEA (12.65 g, 125.0 mmol) andPd(dppf)Cl₂ (3.4 g, 50% wt). The resulting solution was stirred at 80°C. under carbon monoxide atmosphere (50 Psi) for two days. After cooledto room temperature, the mixture was concentrated in vacuum. The residuewas purified by column (PE:EtOAc=100:1) to give compound 3 (4.35 g,69.9%) as a yellow syrup.

¹H NMR: CDCl₃ 400 MHz δ 7.52-7.44 (m, 2H), 7.24 (d, J=7.2 Hz, 1H), 3.91(s, 3H), 2.53 (s, 3H).

Step 3: To a solution of compound 3 (4.35 g, 17.5 mmol) in dry THF (50ml) was added lithium borohydride (1.54 g, 70.0 mmol) in portions at 0°C. under nitrogen. The resulting solution was stirred and refluxed forthree days. The mixture was quenched with water. The resulting solutionwas extracted with EtOAc. The organic phase was dried and concentratedin vacuum to give compound 4 (3.87 g, 100%) as a colorless syrup useddirectly without further purification.

¹H NMR: CDCl₃ 400 MHz δ 7.51-7.47 (m, 2H), 7.30 (d, J=7.6 Hz, 1H), 4.87(s, 2H), 2.50 (s, 3H).

Step 4: To a solution of compound 4 (4.37 g, 19.8 mmol) in dry CH₂Cl₂(50 ml) was added m-CPBA (10.93 g, 79.2 mmol) in portions at 0° C. Theresulting solution was stirred at room temperature for overnight. Themixture was washed with 10% aqueous sodium hydroxide and extracted withCH₂Cl₂. The organic phase was dried and concentrated in vacuum. Theresidue was purified by column (PE/EtOAc: 1/1) to give compound 5 (3.2g, 63.6%)

¹H NMR: CDCl₃ 400 MHz δ 8.29 (d, J=8.0 Hz, 1H), 8.14 (d, J=7.6 Hz, 1H),7.76 (t, J=7.6 Hz, 1H), 4.96 (s, 2H), 3.27 (s, 3H).

Step 5: To a solution of compound 5 (3.2 g, 12.6 mmol) in dry CH₂Cl₂ (35ml) was added dropwise a solution of phosphorus tribromide (5.12 g, 18.9mmol) in CH₂Cl₂ at 0° C. The resulting solution was stirred at roomtemperature for two hours. The mixture was washed with saturated aqueoussodium bicarbonate and extracted with CH₂Cl₂. The organic phase wasdried and concentrated in vacuum to give the crude compound 6 (1.9 g,47.6%) as a yellow solid used directly without further purification.

¹H NMR: CDCl₃ 400 MHz δ 8.35 (d, J=8.0 Hz, 1H), 7.88 (d, J=8.0 Hz, 1H),7.74 (t, J=7.6 Hz, 1H), 4.66 (s, 2H), 3.29 (s, 3H).

Step 6: To a solution of compound 6 (1.9 g, 6.0 mmol) in acetone (20 ml)was added potassium thioacetate (1.03 g, 9.0 mmol) in one portion. Theresulting solution was stirred and refluxed for overnight. The mixturewas filtered and the filtrate was concentrated in vacuum. The residuewas purified by column (PE/EtOAc: 5/1) to give compound 7 (1.55 g,82.9%) as a yellow solid.

¹H NMR: CDCl₃ 400 MHz δ 8.28 (d, J=8.0 Hz, 1H), 7.84 (d, J=8.0 Hz, 1H),7.66 (t, J=8.0 Hz, 1H), 4.37 (s, 2H), 3.27 (s, 3H), 2.37 (s, 3H).

Step 7: To a solution of hydrochloric acid (2M, 0.40 ml) in actonitrile(10 ml) was added NCS (0.85 g, 6.4 mmol) in portions. Then a solution ofcompound 7 (0.50 g, 1.6 mmol) in acetonitrile (1 ml) was added dropwiseat 0° C. The resulting solution was stirred at 0° C. for five minutes.The mixture was concentrated in vacuum. The residue was dissolved inEt₂O and filtered. The filtrate was concentrated in vacuum to givecompound 8 (0.54 g, 100%) as a white solid used directly without furtherpurification.

¹H NMR: CDCl₃ 400 MHz δ 8.53 (d, J=8.0 Hz, 1H), 8.05 (d, J=8.0 Hz, 1H),7.87 (t, J=8.0 Hz, 1H), 5.26 (s, 2H), 3.30 (s, 3H).

Step 8: To a solution of compound 9 (0.35 g, 1.6 mmol) in dry THF (10ml) was added LiHMDS (3.2 ml) dropwise at −78° C. under nitrogen. Afterstirred at −78° C. for 1 hour, a solution of compound 8 (0.54 g, 1.6mmol) in dry THF was added dropwise to the above mixture at −78° C. Theresulting solution was stirred from −78° C. to room temperature forovernight. The mixture was quenched with water. THF was removed byconcentration and the residue was dissolved in water. The resultingaqueous phase was acidified to pH 3 and extracted with EtOAc. Theorganic phase was dried over anhydrous sodium sulfate and concentratedin vacuum. The residue was purified by prep. HPLC to give compound 10(72 mg, 9.3%) as a yellow solid.

¹H NMR: CDCl₃ 400 MHz δ 8.52-8.50 (m, 2H), 7.99 (d, J=7.6 Hz, 1H),7.88-7.81 (m, 2H), 7.61-7.58 (m, 1H), 6.12 (t, J=55.6 Hz, 1H), 4.43-4.31(m, 1H), 4.19-4.08 (m, 1H), 3.27 (s, 3H).

Example 3 Preparation of1-(2,2-difluoroethyl)-3-[3-(2-methoxyethoxy)-2-(trifluoromethyl)phenyl]-2,2-dioxo-pyrido[3,2-c]thiazin-4-ol(hereinafter also referred to as compound 19 which corresponds tocompound I-54 in the Table I below)

Step 1: To a solution of 2-methoxy-ethanol (2.83 g, 37.2 mmol) in DMF(30 ml) was added sodium hydride (1.49 g, 37.2 mmol) in portions at 0°C. under nitrogen. After stirred at room temperature for one hour,compound 11 (3.0 g, 12.4 mmol) was added in one portion. The resultingsolution was stirred at room temperature for one hour. The mixture wasquenched with water, and then poured into EtOAc and water. The solutionwas separated and the organic phase was washed with brine. It was driedand concentrated in vacuum to give the crude compound 12 (3.1 g, 83.5%)as a colorless syrup without further purification.

Step 2: To a solution of compound 12 (5.3 g, 17.7 mmol) intoluene/methanol (300 ml/100 ml) was added TEA (8.95 g, 88.5 mmol, 5 eq)and Pd(dppf)Cl₂ (2.5 g, 50% wt). The resulting solution was stirred at80° C. under carbon monoxide atmosphere (50 Psi.) for two days. Aftercooled to room temperature, the mixture was concentrated in vacuum. Theresidue was purified by column (PE:EtOAc=30:1) to give compound 13 (4.64g, 94.3%) as a yellow syrup.

¹H NMR: CDCl₃ 400 MHz δ 7.50 (t, J=8.0 Hz, 1H), 7.12 (d, J=8.4 Hz, 1H),7.03 (d, J=7.6 Hz, 1H), 4.21 (t, J=4.8 Hz, 2H), 3.90 (s, 3H), 3.78 (t,J=4.8 Hz, 2H), 3.45 (s, 3H).

Step 3: To a solution of compound 13 (4.64 g, 16.7 mmol) in dry THF (50ml) was added lithium borohydride (0.74 g, 33.4 mmol) in portions at 0°C. under nitrogen. The resulting solution was stirred at 70° C. forovernight. The mixture was added dropwise with water. The resultingsolution was extracted with EtOAc. The organic phase was dried andconcentrated in vacuum to give compound 14 (4.0 g, 95.8%) as a yellowsyrup used directly without further purification.

¹H NMR: CDCl₃ 400 MHz δ 7.47 (t, J=8.0 Hz, 1H), 7.26 (d, J=7.6 Hz, 1H),6.99 (d, J=8.4 Hz, 1H), 4.86 (s, 2H), 4.18 (t, J=4.8 Hz, 2H), 3.78 (t,J=5.2 Hz, 2H), 3.46 (s, 3H).

Step 4: To a solution of compound 14 (4.0 g, 16.0 mmol) in dry DCM (50ml) was added dropwise a solution of phosphorus tribromide (6.5 g, 24.0mmol) in DCM at 0° C. The resulting solution was stirred at roomtemperature for two hours. The mixture was washed with saturated aqueoussodium bicarbonate and extracted with DCM. The organic phase was driedand concentrated in vacuum to give the crude compound 15 (3.0 g, 59.9%)as a yellow solid used directly without further purification.

¹H NMR: CDCl₃ 400 MHz δ 7.42 (t, J=8.0 Hz, 1H), 7.05-7.00 (m, 2H), 4.63(s, 2H), 4.18 (t, J=4.8 Hz, 2H), 3.78 (t, J=4.8 Hz, 2H), 3.46 (s, 3H).

Step 5: To a solution of compound 15 (2.0 g, 6.4 mmol) in acetone (20ml) was added potassium thioacetate (1.09 g, 9.6 mmol) in one portion.The resulting solution was stirred and refluxed for overnight. Themixture was filtered and the filtrate was concentrated in vacuum. Theresidue was purified by column (PE/EtOAc: 50/1) to give compound 16(1.74 g, 88.3%) as an orange syrup.

¹H NMR: CDCl₃ 400 MHz δ 7.36 (t, J=8.0 Hz, 1H), 7.09 (d, J=7.6 Hz, 1H),6.95 (d, J=8.4 Hz, 1H), 4.28 (s, 2H), 4.16 (t, J=4.8 Hz, 2H), 3.77 (t,J=4.8 Hz, 2H), 3.45 (s, 3H), 2.32 (s, H).

Step 6: To a solution of hydrochloric acid (2M, 0.5 ml) in actonitrile(10 ml) was added NCS (1.07 g, 8 mmol) in portions. Then a solution ofcompound 16 (0.62 g, 2 mmol) in acetonitrile (1 ml) was added dropwiseat 0° C. The resulting solution was stirred at 0° C. for five minutes.The mixture was concentrated in vacuum. The residue was dissolved inEt₂O and filtered. The filtrate was concentrated in vacuum to givecompound 17 (0.66 g, 100%) as a yellow syrup used directly withoutfurther purification.

¹H NMR: CDCl₃ 400 MHz δ 7.54 (t, J=8.0 Hz, 1H), 7.20 (d, J=8.4 Hz, 1H),7.15 (d, J=7.6 Hz, 1H), 5.19 (s, 2H), 4.22 (t, J=4.8 Hz, 2H), 3.79 (t,J=4.8 Hz, 2H), 3.45 (s, 3H).

Step 7: To a solution of compound 9 (0.32 g, 1.5 mmol) in dry THF (10ml) was added LiHMDS (3 ml) dropwise at −78° C. under nitrogen. Afterstirred at −78° C. for 1 hour, a solution of compound 17 (0.5 g, 1.5mmol) in dry THF was added dropwise to the above mixture at −78° C. Theresulting solution was stirred from −78° C. to room temperature forovernight. The mixture was quenched with water. THF was removed byconcentration and the residue was dissolved in water. The resultingaqueous phase was acidified to pH 3 and extracted with EtOAc. Theorganic phase was dried over anhydrous sodium sulfate and concentratedin vacuo to give the crude product compound 18 (0.61 g, 79.4%) as ayellow syrup used directly without further purification.

Step 8: To a solution of compound 18 (0.61 g, 1.2 mmol) in DMF (6 ml)was added potassium carbonate (0.33 g, 2.4 mmol) in one portion. Theresulting solution was stirred at 110° C. for 2 hours. The mixture wasfiltered and the filtrate was purified by prep. HPLC to give compound 19(117 mg, 20.3%) as a brown solid.

¹H NMR: CDCl₃ 400 MHz δ 8.48 (s, 1H), 7.79 (d, J=8.4 Hz, 1H), 7.60-7.54(m, 2H), 7.25-7.19 (m, 2H) 6.14 (t, J=55.6 Hz, 1H), 4.43-4.31 (m, 1H),4.24 (t, J=4.4 Hz, 2H), 4.23-4.08 (m, 1H), 3.81 (t, J=4.4 Hz, 2H), 3.47(s, 3H).

Example 4 Preparation of3-[5-chloro-3-morpholino-2-(trifluoromethyl)phenyl]-1-(2,2-difluoroethyl)-2,2-dioxo-pyrido[3,2-c]thiazin-4-ol(hereinafter also referred to as compound 29 which corresponds tocompound I-56 in the Table I below)

Step 1: To a solution of compound 20 (80 g, 0.41 mol) in 800 ml AcOH wasadded Br₂ (131 g, 0.82 mol) at room temperature. The mixture was stirredat 50° C. for 5 hrs. The mixture was dilute with CH₂Cl₂ and washed withwater, aq. Na₂CO₃ and brine, the organic layer was dried over Na₂SO₄ andconcentrated in vacuo, the crude product was purified by columnchromatography to give compound 21 (80 g, yield: 55%).

¹H NMR MeOD 400 MHz δ 7.69 (s, 1H).

Step 2: To a solution of compound 21 (40 g, 0.11 mol) in H₃PO₄ (1.2 I)was added dropwise a solution of NaNO₂ (47 g, 0.68 mol) in 200 ml waterat −4° C., H₃PO₂ (480 ml) was added dropwise at −4° C. The resultingmixture was stirred overnight at room temperature The reaction mixturewas diluted with CH₂Cl₂ and neutralized with sat. Na₂CO₃, the organiclayer was washed brine, dried over anhydrous Na₂SO₄ and concentrated invacuo, the crude product was purified by column chromatography to givecompound 22 (30 g, yield: 78%).

¹H NMR MeOD 400 MHz δ 7.93 (s, 2H).

Step 3: A mixture of compound 22 (10 g, 29.6 mmol), morpholine (2.6 g,29.6 mmol), t-BuONa (5.7 g, 59.1 mmol), dppf (1.0 g, 1.77 mmol) andPd₂(dba)₃ (0.81 g, 0.89 mmol) in toluene (150 ml) was heated to 90° C.under N2 atmosphere overnight. The reaction mixture was filtered andconcentrated in vacuo, the residue was purified by column chromatographyto give compound 23 (2.8 g, yield: 25%).

¹ H NMR MeOD 400 MHz δ 7.56 (s, 1H), 7.33 (s, 1H), 3.77-3.79 (m, 4H),2.95-2.97 (m, 4H).

Step 4: PdCl₂(dppf)₂ (1.6 g, 2.2 mmol) was added under N2 atmosphere toa mixture of compound 23 (7.5 g, 21.8 mmol) and TEA (4.4 g, 43.5 mmol)in MeOH (150 mL) and toluene (200 ml) at room temperature. The mixturewas heated to 75° C. at 50 psi under CO atmosphere for overnight. Themixture was filtrated and evaporated in vacuo, the residue was purifiedby column chromatograph (PE:EtOAc=50:1) to give compound 24 (6.2 g,yield: 89%).

¹H NMR: CDCl₃ 400 MHz δ 7.30 (s, 1H), 7.25 (s, 1H), 3.90 (s, 3H),3.81-3.83 (m, 4H), 2.98-3.00 (m, 4H).

Step 5: To a mixture of compound 24 (6.2 g, 19.2 mmol) in 80 ml of THFwas added portionwise LiBH₄ (79 mg, 3.6 mmol) at 0° C. The reactionmixture was stirred at room temperature for 3 days. The mixture wasquenched with water at ice-water and extracted with EtOAc. The organiclayer was washed with brine and dried over anhydrous Na₂SO₄, the crudeproduct was purified by column chromatograph (PE:EtOAc=200:1) to givecompound 25 (3.8 g, yield: 67%).

¹H NMR: CDCl₃ 400 MHz δ 7.48 (s, 1H), 7.12 (s, 1H), 4.78 (s, 2H),3.74-3.76 (m, 4H), 2.82-2.84 (m, 4H).

Step 6: To a solution of compound 25 (3.8 g, 12.9 mmol) in dry CH₂Cl₂(50 ml) was added dropwise a solution of phosphorus tribromide (5.2 g,19.3 mmol) in CH₂Cl₂ (5 ml) at 0° C. The mixture was stirred at roomtemperature for 2 hours. The reaction mixture was poured into saturatedaqueous sodium bicarbonate and adjusted to pH 8 by addition of moresodium bicarbonate. Then it was extracted with CH₂Cl₂ and washed withbrine. The organic phase was dried over anhydrous sodium sulfate andconcentrated in vacuo, the residue was purified by column chromatograph(PE:EtOAc=300:1) to give compound 26 (2.9 g, 63%).

¹H NMR MeOD 400 MHz δ 7.43 (s, 1H), 7.42 (s, 1H), 4.66 (s, 2H),3.78-3.80 (m, 4H), 2.89-2.91 (m, 4H).

Step 7: To a stirred solution of compound 26 (1.0 g, 2.8 mmol) inacetone (10 ml) was added a solution of sodium sulfite (0.39 g, 3.1mmol) in water (10 ml). A white precipitate formed. The reaction mixturewas refluxed overnight, the reaction mixture was concentrated toapproximately one-half of the original column and then filtered. Afterwashing of the filter cake with water was obtained compound 27 (0.94 g,yield: 89%).

¹H NMR DMSO-d6 400 MHz δ 7.49 (s, 1H), 7.40 (s, 1H), 3.92 (s, 2H), 3.66(br, 4H), 2.81 (br, 4H).

Step 8: To a suspension of compound 27 (0.94 g, 2.5 mmol) inacetonitrile (10 ml) under nitrogen was added POCl₃ (2.3 g, 14.8 mmol)at room temperature After refluxing for 6 hrs, the mixture was cooled toroom temperature and dilute with EtOAc, then poured into a mixture ofEtOAc and ice. The organic layer was washed cold water (twice) and brine(twice), and dried over MgSO₄ and concentrated to give compound 28 (0.7g, yield: 75%).

¹H NMR DMSO-d6 400 MHz δ 7.47 (s, 1H), 7.41 (s, 1H), 4.00 (s, 2H), 3.66(br, 4H), 2.81 (br, 4H).

Step 9: LiHMDS (2.2 ml, 2.2 mmol, 1M) was added dropwise to a solutionof compound 9 (0.24 g, 1.1 mmol) in THF at −78° C. under N2 atmosphere,the mixture was continued to stir for 2 hrs at −78° C., then compound 28(0.38 g, 1.1 mmol) in THF was added dropwise to the above mixture, theresulting mixture was stirred for overnight at room temperature Themixture was quenched with H₂O and acidified to pH 3 with aq. HCl, thereaction mixture was extracted with EtOAc and washed with brine. Theorganic layer was dried over anhydrous Na₂SO₄ and concentrated in vacuo.The crude product was purified by pre-HPLC to give compound 29 (250 mg,yield: 36%)

¹H NMR: CDCl₃ 400 MHz δ 8.45 (d, 1H, J=4.8 Hz), 7.75 (d, 1H, J=8.4 Hz),7.50-7.54 (m, 1H), 7.40 (s, 1H), 7.39 (s, 1H), 6.03-6.34 (m, 1H),4.28-4.32 (m, 1H), 4.05-4.10 (m, 1H), 3.75-3.78 (m, 4H), 2.88-2.90 (m,4H).

TABLE I Compounds of the formula I.1A-1 I.1A-1

LCMS No. R^(X) R¹ R² R³ R⁴ R⁵ R⁷ R⁸ R^(A) m/z I-1 CH₂CHF₂ CF₃ H H H H HH H 406.3 I-2 CH₂CHF₂ CF₃ H H Cl H H H H 441.1 I-3 CH₂CHF₂ CF₃ H H F H HH H 425.0 I-4 H CF₃ H H H H H H H 342.3 I-5 CH₂CHF₂ Cl H H H H H H H373.0 I-6 CH₂CHF₂ NO₂ H H H H H H H 384.0 I-7 CH₂CHF₂ Cl H H Cl H H H H407.2 I-8 CH₂CHF₂ Me 3-Me-isoxazolin- SO₂Me H H H H H 514.0 5-yl I-9CH₂CHF₂ Cl OCF₃ H H H H H H 456.8 I-10 CH₂CHF₂ Me SO₂CH₂CH₂C(Me₂) H H HH H 484.5 I-11 CH₂CHF₂ Me Ph H H H H H H 428.5 I-12 CH₂CHF₂ Cl H Cl H HH H H 406.9 I-13 Et Cl H H H H H H H 337.0 I-14 Et CF₃ H H H H H H H371.0 I-15 2-Me-Pr Me SO₂CH₂CH₂C(NOMe) H H H H H 491.6 I-16 n-Pr Cl H HH H H H H 351.0 I-17 n-Bu Cl H H H H H H H 365.0 I-18 2-Me-Pr Cl H H H HH H H 365.0 I-19 n-Pr CF₃ H H H H H H H 385.0 I-20 n-Bu CF₃ H H H H H HH 399.0 I-21 2-Me-Pr CF₃ H H H H H H H 399.0 I-22 CH₂CHF₂ MeSO₂CH₂CH₂C(NOMe) H H H H H 499.5 I-23 CH₂CHF₂ Cl OEt SO₂Et H H H H H508.9 I-24 n-Pr Cl OCF₃ H H H H H H 434.8 I-25 n-Bu Cl OCF₃ H H H H H H448.8 I-26 2-Me-Pr Cl OCF₃ H H H H H H 449.0 I-27 CH₂CHF₂ Me OMe SO₂Me HH H H H 461.0 I-28 n-Bu Cl OEt SO₂Et H H H H H 501.0 I-29 2-Me-Pr Cl OEtSO₂Et H H H H H 501.0 I-30 Et Me OMe SO₂Me H H H H H 424.5 I-31 n-Pr MeOMe SO₂Me H H H H H 438.5 I-32 n-Bu Me OMe SO₂Me H H H H H 452.5 I-332-Me-Pr Me OMe SO₂Me H H H H H 452.5 I-34 Et Cl OCF₃ H H H H H H 420.8I-35 CH₂CHF₂ Cl 3-Me-isoxazolin- Cl H H H H H 490.0 5-yl I-36 CH₂CHF₂ ClMe SO₂Me H H H H H 465.9 I-37 CH₂CHF₂ Me CN SO₂Me H H H H H 457.0 I-38CH₂CHF₂ Cl OMe SO₂Me H H H H H 480.9 I-39 Me Cl H Cl H H H H H 356.9I-40 Et Cl H Cl H H H H H 370.9 I-41 n-Pr Cl H Cl H H H H H 385.0 I-42n-Bu Cl H Cl H H H H H 399.0 I-43 2-Me-Pr Cl H Cl H H H H H 399.0 I-44Me Cl H H H H H H H 322.8 I-45 Me CF₃ H H H H H H H 357.0 I-46 CH₂CHF₂Cl C(O)C(Me₂)CH₂SO₂ H H H H H 505.0 I-47 2-Me-Pr Me SO₂CH₂CH₂C(Me₂) H HH H H 476.6 I-48 CH₂CHF₂ Cl CH₂CH₂SO₂ H H H H H 462.9 I-49 2-Me-Pr Me PhH H H H H H 420.5 I-50 CH₂CHF₂ Me NC(Cl)S H H H H H 443.9 I-51 i-Pr Cl HH H H H H H 350.8 I-52 i-Pr CF₃ H H H H H H H 384.4 I-53 2-Me-Pr ClCH₂CH₂SO₂ H H H H H 455.0 I-54 CH₂CHF₂ CF₃ OCH₂CH₂OMe H H H H H H 480.9I-55 CH₂CHF₂ CF₃ OCH₂- H H H H H H 507.1 (tetrahydrofuran- 2-yl) I-56CH₂CHF₂ CF₃ morpholin-4-yl H Cl H H H H 525.8 I-57 CH₂CHF₂ Br H H H H HH H 418.9 I-58 CH₂CHF₂ Cl Me Cl H H H H H 421.2 I-59 Et Cl Me Cl H H H HH 385.3 I-60 CH₂CHF₂ Cl CHCHCHCH H H H H H 423.0 I-61 Et Cl CHCHCHCH H HH H H 387.0 I-62 CH₂CHF₂ F H F H H H H H 375.0 I-63 Et F H F H H H H H339.0 I-64 CH₂CHF₂ Me isoxazolin-3-yl OCHF₂ H H H H H 488.0 I-65 CH₂CHF₂Cl 3-Me-isoxazolin- SO₂Me H H H H H 534.0 5-yl I-66 CH₂CHF₂ Clisoxazolin-3-yl SO₂Me H H H H H 519.9 I-67 Et Me C(O)C(Me₂)CH₂SO₂ H H HH H 462.5 I-68 n-Pr Me C(O)C(Me₂)CH₂SO₂ H H H H H 476.6 I-69 n-Bu MeC(O)C(Me₂)CH₂SO₂ H H H H H 490.6 I-70 2-Me-Pr Me C(O)C(Me₂)CH₂SO₂ H H HH H 490.6 I-71 CH₂CHF₂ Me C(O)C(Me₂)CH₂SO₂ H H H H H 498.5 I-72 CH₂CHF₂CO₂Me H H H H H H H 397.0 I-73 CH₂CH(OEt)₂ Cl H H H H H H H 425.0 I-74CH₂CHF₂ Cl Cl OMe H H H H H 436.9 I-75 Et Cl 3-Me-isoxazolin- Cl H H H HH 454.0 5-yl I-76 CH₂CHF₂ F H H H H H H H 357.0 I-77 Et Br H H H H H H H383.9 I-78 CH₂CHF₂ CF₃ H Cl H H H H H 440.8 I-79 CH₂CHF₂ Cl H I H H H HH 498.9 I-80 CH₂CHF₂ Cl H H I H H H H 498.9 I-81 Et Cl H Br H H H H H415.0 I-82 CH₂CH(OMe)₂ CF₃ H H H H H H H 430.9 I-83 CH₂CHF₂ Me SO₂MeSO₂Me H H H H H 508.5 I-84 Et Me SO₂Me SO₂Me H H H H H 472.6 I-85CH₂CHF₂ CF₃ H H Cl F H H H 458.9 I-86 H H H H H H H H H 274.3 I-87CH₂CHF₂ Cl H Cl F H H H H 424.9 I-88 Et Cl H Cl F H H H H 388.9 I-89CH₂CHF₂ CN H H H H H H H 363.3 I-90 Et CN H H H H H H H 327.0 I-91CH₂CHF₂ Me 3-Me-isoxazolin- Cl H H H H H 470.0 5-yl I-92 CH₂CHF₂ CF₃ PhH H H H H H 483.0 I-93 CH₂CHF₂ Cl H H H Cl H H H 406.9 I-94 CH₂CHF₂ Cl HF H H H H H 391.0 I-95 Et Cl H H H Cl H H H 370.9 I-96 Et Cl H F H H H HH 355.0 I-97 Et Cl iPr H H H H H H 379.0 I-98 CH₂CHF₂ Cl iPr H H H H H H415.0 I-99 CH₂CHF₂ Me Br H H H H H H 432.9 I-100 Et Me Br H H H H H H396.9 I-101 CH₂CHF₂ I H H H H H H H 464.9 I-102 CH₂CH(OMe)₂ Cl H Cl H HH H H 431.1 I-103 CH₂CHF₂ Me H H H H H H H 353.0 I-104 CH₂CHF₂ Br H Cl HH H H H 452.9 I-105 CH₂CHF₂ Cl Cy-Hex H H H H H H 455.0 I-106 CH₂CHF₂ Clt-Bu H H H H H H 429.0 I-107 CH₂CHF₂ Cl Ph H H H H H H 449.0 I-108CH₂CHF₂ Cl Me F H H H H H 405.0 I-109 CH₂CHF₂ OMe 3-Me-isoxazolin- SO₂MeH H H H H 529.5 5-yl I-110 Et Br H Cl H H H H H 415.7 I-111 Et Cl Cy-HexH H H H H H 418.9 I-112 Et Cl t-Bu H H H H H H 392.9 I-113 Et Cl Me F HH H H H 368.8 I-114 Et Cl Ph H H H H H H 412.9 I-115 CH₂CHF₂ Cl3-Cl-6-OMe- H H H H H H 513.0 phenyl I-116 Et Cl 3-Cl-6-OMe- H H H H H H477.4 phenyl I-117 Et CF₃ H H H F H H H 389.2 I-118 CH₂CHF₂ CF₃ H H H FH H H 425.2 I-119 CH₂CHF₂ Cl H Br H H H H H 451.1 I-120 CH₂CHF₂ Cl3-Me-isoxazolin- Cl H H H H H 488.0 5-yl I-121 CH₂CHF₂ Cl CF₃ H H H H HH 440.9 I-122 CH₂CHF₂ OCF₃ H H H H H H H 423.0 I-123 CH₂CHF₂ H H H H H HH H 339.0 I-124 Et Cl CF₃ H H H H H H 405.0 I-125 Et OCF₃ H H H H H H H387.0 I-126 CH₂CHF₂ Cl Cl H H H H H H 406.9 I-127 Et Cl Cl H H H H H H371.0 I-128 CH₂CHF₂ Cl Me H H H H H H 387.0 I-129 Et Cl Me H H H H H H350.8 I-130 n-Pr Cl H Cl H H H OMe H 415.3 I-131 Et Cl H Cl H H H OMe H401.0 I-132 CH₂CHF₂ CF₃ H H Cl Cl H H H 474.9 I-133 Et Cl H Cl H H Cl HH 406.9 I-134 Et Cl H Cl H H CO₂Me H H 428.9 I-135 CH₂CH₂OH CF₃ H H H HH H H 387.2 I-136 CH₂CH₂OH Cl H Cl H H H H H 387.1 I-137 CH₂CHF₂ OCF₂CF₃H H H H H H H 473.0 I-138 Et OCF₂CF₃ H H H H H H H 437.0 I-139 Et Br H HCl H H H H 417.1 I-140 CH₂CHF₂ Br H H Cl H H H H 452.9 I-141 Et Cl H H FH H H H 355.1 I-142 CH₂CHF₂ Cl H H F H H H H 391.1 I-143 Allyl CF₃ H H HH H H H 383.2 I-144 Allyl Cl H Cl H H H H H 383.1 I-145 Et Cl H CO₂Me HH H H H 395.1 I-146 Et I H F H H H H H 447.0 I-147 Et I H SO₂Me H H H HH 487.1 I-148 CH₂CHF₂ CF₃ SO₂Me H H H H H H 485.1 I-149 Et CF₃ SO₂Me H HH H H H 449.2 I-150 CH₂CHF₂ Cl oxolan-2-yl Cl H H H H H 478.9 I-151 EtCl oxolan-2-yl Cl H H H H H 443.3 I-152 CH₂CHF₂ Cl 3-Me-isoxazolin- Cl HH H H COiPr 560.4 5-yl I-153 CH₂CHF₂ Cl 3-Me-isoxazolin- Cl H H H HCOtBu 574.4 5-yl I-154 CH₂CHF₂ Cl 3-Me-isoxazolin- Cl H H H H SO₂Me568.4 5-yl I-155 CH₂CF₃ Cl 3-Me-isoxazolin- Cl H H H H H 507.9 5-ylI-156 Et Cl 3-Me-isoxazolin- Cl H H H H H 452.3 5-yl I-157 Et Cl3-Me-isoxazolin- SO₂Me H H H H H 498.0 5-yl I-158 Et H H H H H H H H303.0 I-159 Et I H H H H H H H 428.9 I-160 Et Cl Me SO₂Me H H H H H429.0 I-161 Me I H H H H H H H 414.9 I-162 CH₂CF₃ Cl H F H H H H H 408.9I-163 CH₂CF₃ Cl H Cl F H H H H 442.9 I-164 CH₂CHF₂ Cl SO₂Me H H Cl H H H484.9 I-165 Et Cl SO₂Me H H Cl H H H 449.3 I-166 CH₂CF₃ Cl H H H H H H H390.9 I-167 CH₂CF₃ Br H H H H H H H 434.9 I-168 Et Cl H CO₂Et H H H H H409.2 I-169 Et I H CO₂Et H H H H H 501.1 I-170 CH₂CHF₂ H Cl H Cl H H H H407.2 I-171 CH₂CHF₂ Cl H H H F H H H 390.8 I-172 CH₂CH(OMe)₂ Cl H Cl H HCl H H 465.7 I-173 Et Cl H Cl H Cl H H H 405.9 I-174 CH₂CHF₂ Cl H Cl HCl H H H 442.9 I-175 Et Br H F H H H H H 400.9 I-176 CH₂CHF₂ Br H F H HH H H 435.9 I-177 Et CF₃ H H Cl H H H H 405.1 I-178 Et Br H Br H H H H H461.0 I-179 Et I Cl H Cl H H H H 496.9 I-180 Et I H Br F H H H H 525.0I-181 CH₂CF₃ Me Br H H H H H H 450.9 I-182 CH₂CHF₂ Cl OEt Cl H F H H H468.9 I-183 CH₂CF₃ I H H H H H H H 482.9 I-184 Et CF₃ H F H H H H H389.1 I-185 CH₂CHF₂ CF₃ H F H H H H H 425.2 I-186 Et CF₃ H Br H H H H H450.9 I-187 Et I H H Cl H H H H 463.0 I-188 Et I H Br H H H H H 508.8I-189 CH₂CHF₂ Cl CN Cl H H H H H 432.2 I-190 Et Cl isoxazolin-3-yl Cl HH H H H 440.3 I-191 Et Cl CH₂OCH₂CF₃ Cl H H H H H 483.3 I-192 Et Cl3-Me-isoxazolin- Cl H H H H H 454.3 5-yl I-193 Et Cl SO₂CH₂CH₂C(Me₂) H HH H H 469.0 I-194 CH₂CF₃ CF₃ H H H H H H H 424.3 I-195 CH₂CHF₂ Clisoxazolin-3-yl Cl H H H H H 476.3 I-196 CH₂CHF₂ Cl CH₂OCH₂CF₃ Cl H H HH H 519.3 I-197 CH₂CHF₂ Cl 3-Me-isoxazolin- Cl H H H H H 490.3 5-ylI-198 CH₂CHF₂ CF₃ H Br H H H H H 485.9 I-199 CH₂CHF₂ I H Cl H H H H H499.1 I-200 CH₂CHF₂ Cl Cl H H Cl H H H 441.1 I-201 Et CF₃ H H H Cl H H H405.0 I-202 CH₂CHF₂ CF₃ H H H Cl H H H 441.1 I-203 Et Cl Cl H Cl H H H H406.9 I-204 CH₂CHF₂ Cl Cl H Cl H H H H 441.1 I-205 Et Cl Cl H H Cl H H H407.0 I-206 Et Cl Br H H H H H H 415.9 I-207 Et I H Cl H H H H H 463.0I-208 CH₂CF₃ Cl H Cl H H H H H 425.2 I-209 CH₂CHF₂ Cl H NO₂ H H H H H417.8 I-210 Et Cl H NO₂ H H H H H 381.8 I-211 CH₂CHF₂ Cl H Cl Cl H H H H441.7 I-212 CH₂CF₃ Cl H Cl Cl H H H H 459.7 I-213 CH₂CF₃ Cl Cl H H Cl HH H 459.7 I-214 CH₂CF₃ CF₃ H H Cl F H H H 476.8 Wherein Me denotesmethyl, Et denotes ethyl, Pr denotes propyl, i-Pr denotes iso-propyl, Budenotes butyl, t-Bu denotes tert-butyl, Ph denotes phenyl and Cy-Hexdenotes cyclohexyl

II. USE EXAMPLES

The herbicidal activity of the compounds of the formula I wasdemonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, which had beensuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtransparent plastic hoods until the plants had rooted. This cover causeduniform germination of the test plants, unless this has been impaired bythe active ingredients.

For the post-emergence treatment, the test plants were first grown to aheight of 3 to 15 cm, depending on the plant habit, and only thentreated with the active ingredients which had been suspended oremulsified in water. For this purpose, the test plants were either sowndirectly and grown in the same containers, or they were first grownseparately as seedlings and transplanted into the test containers a fewdays prior to treatment.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialmoieties, and 0 means no damage, or normal course of growth. A goodherbicidal activity is given at values of at least 70 and a very goodherbicidal activity is given at values of at least 85.

The plants used in the greenhouse experiments belonged to the followingspecies:

Bayer Code Scientific name English name ABUTH Abutilon theophrastivelvetleaf ALOMY Alopecurus myosuroides blackgrass AMARE Amaranthusretroflexus common amaranth AVEFA Avena fatua wild oat CHEAL Chenopodiumalbum lampsquaters ECHCG Echinochloa crus-galli comon barnyardgrassGALAP Galium aparine goosegrass SETFA Setaria faberi Faber's foxtailSETVI Setaria viridis green foxtail STEME Stellaria media commonchickweed

At an application rate of 0.5 kg/ha, the compounds I-28 and I-46,applied by the post-emergence method, showed very good herbicidalactivity against ABUTH.

At an application rate of 0.25 kg/ha, the compound I-45, applied by thepost-emergence method, showed very good herbicidal activity againstABUTH.

At an application rate of 0.5 kg/ha, the compound I-7, applied by thepost-emergence method, showed very good herbicidal activity againstALOMY.

At an application rate of 0.25 kg/ha, the compound I-82, applied by thepost-emergence method, showed very good herbicidal activity againstALOMY.

At an application rate of 0.5 kg/ha, the compounds I-1, I-2, I-12, I-36,I-37, I-39, I-40, I-41, I-42, I-64, I-101, I-109, I-118 and I-119,applied by the post-emergence method, showed very good herbicidalactivity against AMARE.

At an application rate of 0.5 kg/ha, the compounds I-43, I-104 andI-108, applied by the post-emergence method, showed good herbicidalactivity against AMARE.

At an application rate of 0.447 kg/ha, the compound I-8, applied by thepost-emergence method, showed very good herbicidal activity againstAMARE.

At an application rate of 0.25 kg/ha, the compounds I-38, I-55, I-63,I-65, I-67, I-71, I-75, I-77, I-78 and I-79, applied by thepost-emergence method, showed very good herbicidal activity againstAMARE.

At an application rate of 0.25 kg/ha, the compound I-56, applied by thepost-emergence method, showed good herbicidal activity against AMARE.

At an application rate of 0.154 kg/ha, the compound I-29, applied by thepost-emergence method, showed very good herbicidal activity againstAMARE.

At an application rate of 0.075 kg/ha, the compound I-66, applied by thepost-emergence method, showed very good herbicidal activity againstAMARE.

At an application rate of 0.041 kg/ha, the compound I-10, applied by thepost-emergence method, showed very good herbicidal activity againstAMARE.

At an application rate of 0.5 kg/ha, the compounds I-15, I-27 and I-35applied by the post-emergence method, showed very good herbicidalactivity against AVEFA.

At an application rate of 0.5 kg/ha, the compounds I-1, I-2, I-3, I-5,I-12, I-36, I-37, I-39, I-40, I-41, I-42, I-43, I-50, I-51, I-61, I-64,I-73, I-87, I-91, I-93, I-94, I-98, I-101, I-104, I-108, I-109, I-118,I-119 and I-120, applied by the post-emergence method, showed very goodherbicidal activity against CHEAL.

At an application rate of 0.447 kg/ha, the compound I-8, applied by thepost-emergence method, showed very good herbicidal activity againstCHEAL.

At an application rate of 0.4 kg/ha, the compounds I-32 and I-33,applied by the post-emergence method, showed very good herbicidalactivity against CHEAL.

At an application rate of 0.345 kg/ha, the compound I-33, applied by thepost-emergence method, showed very good herbicidal activity againstCHEAL.

At an application rate of 0.25 kg/ha, the compounds I-23, I-38, I-55,I-56, I-63, I-65, I-67, I-75, I-77, I-78, I-79, I-81, I-83 and I-85,applied by the post-emergence method, showed very good herbicidalactivity against CHEAL.

At an application rate of 0.25 kg/ha, the compound I-71, applied by thepost-emergence method, showed good herbicidal activity against CHEAL.

At an application rate of 0.233 kg/ha, the compound I-34, applied by thepost-emergence method, showed very good herbicidal activity againstCHEAL.

At an application rate of 0.2 kg/ha, the compound I-50, applied by thepost-emergence method, showed very good herbicidal activity againstCHEAL.

At an application rate of 0.154 kg/ha, the compounds I-29, I-50 andI-59, applied by the post-emergence method, showed very good herbicidalactivity against CHEAL.

At an application rate of 0.1 kg/ha, the compounds I-44 and I-53,applied by the post-emergence method, showed very good herbicidalactivity against CHEAL.

At an application rate of 0.075 kg/ha, the compound I-66, applied by thepost-emergence method, showed very good herbicidal activity againstCHEAL.

At an application rate of 0.0625 kg/ha, the compound I-62, applied bythe post-emergence method, showed very good herbicidal activity againstCHEAL.

At an application rate of 0.041 kg/ha, the compound I-10, applied by thepost-emergence method, showed very good herbicidal activity againstCHEAL.

At an application rate of 0.5 kg/ha, the compound I-3, applied by thepost-emergence method, showed very good herbicidal activity againstECHCG.

At an application rate of 0.5 kg/ha, the compound I-5, applied by thepost-emergence method, showed good herbicidal activity against ECHCG.

At an application rate of 0.4 kg/ha, the compounds I-32 and I-33,applied by the post-emergence method, showed very good herbicidalactivity against ECHCG.

At an application rate of 0.345 kg/ha, the compound I-33, applied by thepost-emergence method, showed very good herbicidal activity againstECHCG.

At an application rate of 0.25 kg/ha, the compounds I-52, I-65 and I-67,applied by the post-emergence method, showed very good herbicidalactivity against ECHCG.

At an application rate of 0.1 kg/ha, the compound I-44, applied by thepost-emergence method, showed very good herbicidal activity againstECHCG.

At an application rate of 0.5 kg/ha, the compound I-7, applied by thepost-emergence method, showed good herbicidal activity against GALAP.

At an application rate of 0.25 kg/ha, the compounds I-24 and I-55,applied by the post-emergence method, showed very good herbicidalactivity against GALAP.

At an application rate of 0.0625 kg/ha, the compound I-62, applied bythe post-emergence method, showed good herbicidal activity againstGALAP.

At an application rate of 0.5 kg/ha, the compounds I-11, I-15, I-27,I-31, I-35 and I-48, applied by the post-emergence method, showed verygood herbicidal activity against SETFA.

At an application rate of 0.5 kg/ha, the compound I-22, applied by thepost-emergence method, showed good herbicidal activity against SETFA.

At an application rate of 0.5 kg/ha, the compounds I-2, I-3, I-50, I-51,I-87, I-91, I-93 and I-94, applied by the post-emergence method, showedvery good herbicidal activity against SETVI.

At an application rate of 0.5 kg/ha, the compounds I-1, I-5 and I-12,applied by the post-emergence method, showed good herbicidal activityagainst SETVI.

At an application rate of 0.25 kg/ha, the compounds I-75, I-78, I-79,I-80, I-83 and I-85, applied by the post-emergence method, showed verygood herbicidal activity against STEME.

At an application rate of 0.25 kg/ha, the compounds I-77 and I-81,applied by the post-emergence method, showed good herbicidal activityagainst STEME.

At an application rate of 0.233 kg/ha, the compound I-34, applied by thepost-emergence method, showed very good herbicidal activity againstSTEME.

At an application rate of 0.075 kg/ha, the compound I-66, applied by thepost-emergence method, showed very good herbicidal activity againstSTEME.

1-15. (canceled)
 16. A substituted pyridine of the formula I

in which the variables have the following meaning: R is O—R^(A),S(O)_(n)—R^(A) or O—S(O)_(n)—R^(A); R^(A) is hydrogen, C₁-C₄-alkyl,Z—C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl,Z—C₃-C₆-cycloalkenyl, C₂-C₆-alkynyl, Z-(tri-C₁-C₄-alkyl)silyl,Z—C(═O)—R^(a), Z—NR^(i)—C(O)—NR^(i)R^(ii), Z—P(═O)(R^(a))₂,NR^(i)R^(ii), a 3- to 7-membered monocyclic or 9- or 10-memberedbicyclic saturated, unsaturated or aromatic heterocycle which contains1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N andS and which may be partially or fully substituted by groups R^(a) and/orR^(b), R^(a) is hydrogen, OH, C₁-C₈-alkyl, C₁-C₄-haloalkyl,Z—C₃-C₆-cycloalkyl, C₂-C₈-alkenyl, Z—C₅-C₆-cycloalkenyl, C₂-C₈-alkynyl,Z—C₁-C₆-alkoxy, Z—C₁-C₄-haloalkoxy, Z—C₃-C₈-alkenyloxy,Z—C₃-C₈-alkynyloxy, NR^(i)R^(ii), C₁-C₆-alkylsulfonyl,Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl, Z-phenoxy, Z-phenylamino or a 5- or6-membered monocyclic or 9- or 10-membered bicyclic heterocycle whichcontains 1, 2, 3 or 4 heteroatoms selected from the group consisting ofO, N and S, where the cyclic groups are unsubstituted or substituted by1, 2, 3 or 4 groups R^(b); R^(i), R^(ii) independently of one anotherare hydrogen, C₁-C₈-alkyl, C₁-C₄-halo-alkyl, C₃-C₈-alkenyl,C₃-C₈-alkynyl, Z—C₃-C₆-cycloalkyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy,Z—C(═O)—R^(a), Z-phenyl, a 3- to 7-membered monocyclic or 9- or10-membered bicyclic saturated, unsaturated or aromatic heterocyclewhich contains 1, 2, 3 or 4 heteroatoms selected from the groupconsisting of O, N and S and which is attached via Z; or R^(i) andtogether with the nitrogen atom to which they are attached may form a 5-or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle whichcontains 1, 2, 3 or 4 heteroatoms selected from the group consisting ofO, N and S; R^(b) independently of one another are Z—CN, Z—OH, Z—NO₂,Z-halogen, oxo (═O), ═N—R^(a), C₁-C₈-alkyl, C₁-C₄-haloalkyl,C₂-C₈-alkenyl, C₂-C₈-alkynyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy,Z—C₃-C₁₀-cycloalkyl, O—Z—C₃-C₁₀-cycloalkyl, Z—C(═O)—R^(a), NR^(i)R^(ii),Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl or S(O)_(n)R^(bb); or two groupsR^(b) may together form a ring which has three to six ring members and,in addition to carbon atoms, may also contain heteroatoms from the groupconsisting of O, N and S and may be unsubstituted or substituted byfurther groups R^(b); R^(bb) is C₁-C₈-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl or C₁-C₆-haloalkyl;Z is a covalent bond or C₁-C₄-alkylene; n is 0, 1 or 2; R¹ is cyano,halogen, nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-haloalkyl, Z—C₁-C₆-alkoxy, Z—C₁-C₄-alkoxy-C₁-C₄-alkoxy,Z—C₁-C₄-alkylthio, Z—C₁-C₄-alkylthio-C₁-C₄-alkylthio, C₂-C₆-alkenyloxy,C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy,S(O)_(n)R^(bb), Z-phenoxy, or Z-heterocyclyloxy, where heterocyclyl is a5- or 6-membered monocyclic or 9- or 10-membered bicyclic saturated,partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or4 heteroatoms selected from the group consisting of O, N and S, wherecyclic groups are unsubstituted or partially or fully substituted byR^(b); A is N or C—R²; R², R³, R⁴, R⁵ independently of one another arehydrogen, Z-halogen, Z—CN, Z—NO₂, C₁-C₈-alkyl, C₁-C₄-haloalkyl,C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₂-C₈-haloalkenyl, C₂-C₈-haloalkynyl,Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy, Z—C₁-C₄-alkoxy-C₁-C₄-alkoxy,Z—C₁-C₄-alkylthio, Z—C₁-C₄-alkylthio-C₁-C₄-alkylthio,Z—C₁-C₆-haloalkylthio, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,C₁-C₆-haloalkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy, Z—C₃-C₁₀-cycloalkyl,O—Z—C₃-C₁₀-cycloalkyl, Z—C(═O)—R^(a), NR^(i)R^(ii),Z-(tri-C₁-C₄-alkyl)silyl, S(O)_(n)R^(bb), Z-phenyl, Z¹-phenyl,Z-heterocyclyl, or Z¹-heterocyclyl, where heterocyclyl is a 5- or6-membered monocyclic or 9- or 10-membered bicyclic saturated, partiallyunsaturated or aromatic heterocycle which contains 1, 2, 3 or 4heteroatoms selected from the group consisting of O, N and S, wherecyclic groups are unsubstituted or partially or fully substituted byR^(b); or R² together with the group attached to the adjacent carbonatom may also form a five- to ten-membered saturated or partially orfully unsaturated mono- or bicyclic ring which, in addition to carbonatoms, may contain 1, 2 or 3 heteroatoms selected from the groupconsisting of O, N and S and may be substituted by further groups R^(b);Z¹ is a covalent bond, C₁-C₄-alkyleneoxy, C₁-C₄-oxyalkylene orC₁-C₄-alkyleneoxy-C₁-C₄-alkylene; R⁶ is hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkoxy, orC₁-C₄-haloalkylthio; R⁷, R⁸ independently of one another are hydrogen,halogen or C₁-C₄-alkyl; R^(x) is C₁-C₆-alkyl, C₁-C₄-haloalkyl,C₁-C₂-alkoxy-C₁-C₂-alkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₃-C₆-alkynyl, C₃-C₆-haloalkynyl or Z-phenyl, which is unsubstituted orsubstituted by 1 to 5 groups R^(b); where in the groups R^(A), and R¹,R², R³, R⁴ and R⁵ and their substituents, the carbon chains and/or thecyclic groups may be partially or fully substituted by groups R^(b), oran N-oxide or an agriculturally suitable salt thereof.
 17. The compoundof claim 17 in which A is CR².
 18. The compound of claim 17 in which R²is an optionally substituted five- or six-membered saturated, partiallyunsaturated or aromatic heterocycle which contains 1, 2, 3 or 4heteroatoms selected from the group consisting of O, N and S.
 19. Thecompound of claim 17 in which R² is

in which # denotes the bond through which the group R² is attached and:R^(P2) is H or F; R^(P3) is H, F, Cl or OCH₃; and R^(P4) is H, F, Cl,CH₃, CF₃, OCH₃, OCH₂OCH₃ or OCH₂CH₂OCH₃.
 20. The compound of claim 19 inwhich R² is an optionally R^(b)-substituted heterocycle selected fromthe group consisting of isoxazoline, tetrazolone,1,2-dihydrotetrazolone, 1,4-dihydrotetrazolone, tetrahydrofuran,dioxolane, piperidine, morpholine, piperazine, isoxazole, pyrazole,thiazole, oxazole, furyl, pyridine and pyrazine, and R^(b) is selectedfrom the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-alkylthio-C₁-C₄-alkyl.
 21. Thecompound of claim 17 in which R² is an aliphatic group selected from thegroup consisting of C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₂-C₄-alkoxy, C₂-C₄-haloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy,C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₄-alkoxycarbonyl,S(O)₂—C₁-C₈-alkyl and S(O)₂—C₁-C₈-haloalkyl.
 22. The compound of claim16 in which R¹ is halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio orC₁-C₄-alkylsulfonyl; and R³ is H, halogen, CN, NO₂, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, orC₁-C₄-alkylsulfonyl.
 23. The compound of claim 17 in which R² togetherwith R¹ or R³ forms an optionally R^(b)-substituted five- toten-membered mono- or bicyclic, partially unsaturated ring whichcontains 1, 2, 3 or 4 heteroatoms selected from the group consisting ofO, N and S.
 24. The compound of claim 23 in which the ring substitutedby groups R¹, R², R³ and R⁴ corresponds to one of groups A to L


25. The compound of claim 16 in which A is N and R¹ is nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio or C₁-C₄-alkylsulfonyl; and R³ isH, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthioor C₁-C₄-alkylsulfonyl.
 26. The compound of claim 16 in which X, Yindependently of one another are O or S; R⁴, R⁵ are H, Cl or F; and R⁶,R⁷ are H.
 27. The compound of claim 16 in which R⁴ and R⁵ are hydrogen.28. The compound of claim 17 in which the groups R¹, R², R³, R⁴ and R⁵together form the following substitution patterns: 2-Br, 2-Cl, 2,4-Cl₂,2-Cl-4-F, 2-Cl-5-F, 2-Cl-6-F, 2-Cl-4-CF₃, 2-Cl-5-CF₃, 2-Cl-6-CF₃,2-Cl-3,6-F₂, 2-F, 2,4-F₂, 2,5-F₂, 2,6-F₂, 2-F-4-CF₃, 2-F-5-CF₃,2-F-6-CF₃, 2,3,6-F₃, 2-NO₂, 2-NO₂-4-F, 2-NO₂-5-F, 2-NO₂-6-F,2-NO₂-4-CF₃, 2-NO₂-5-CF₃, 2-NO₂-6-CF₃, 2-NO₂-3,6-F₂, 2-CN, 2-CH₃,2-CH₃-4-F, 2-CH₃-5-F, 2-CH₃-6-F, 2-CH₃-4-CF₃, 2-CH₃-5-CF₃, 2-CH₃-6-CF₃,2-CH₃-3,6-F₂, 2-OCH₃, 2-OCH₃-4-F, 2-OCH₃-5-F, 2-OCH₃-6-F, 2-OCH₃-4-CF₃,2-OCH₃-5-CF₃, 2-OCH₃-6-CF₃, 2-OCH₃-3,6-F₂, 2-CHF₂, 2-CHF₂-4-F,2-CHF₂-5-F, 2-CHF₂-6-F, 2-CHF₂-4-CF₃, 2-CHF₂-5-CF₃, 2-CHF₂-6-CF₃,2-CHF₂-3,6-F₂, 2-CF₃, 2-CF₃-4-F, 2-CF₃-5-F, 2-CF₃-6-F, 2-CF₃-4-CF₃,2-CF₃-5-CF₃, 2-CF₃-6-CF₃, 2-CF₃-3,6-F₂, 2-OCHF₂, 2-OCHF₂-4-F,2-OCHF₂-5-F, 2-OCHF₂-6-F, 2-OCHF₂-4-CF₃, 2-OCHF₂-5-CF₃, 2-OCHF₂-6-CF₃,2-OCHF₂-3,6-F₂, 2-OCF₃, 2-OCF₃-4-F, 2-OCF₃-5-F, 2-OCF₃-6-F,2-OCF₃-4-CF₃, 2-OCF₃-5-CF₃, 2-OCF₃-6-CF₃, 2-OCF₃-3,6-F₂, 2-Cl-3-Br-6-F,2-Cl-5-CF₃, 2,5,6-Cl₃ or 2-CF₃-5-Cl.
 29. A composition comprising aherbicidally effective amount of at least one compound of claim 16 andauxiliaries customary for formulating crop protection agents.
 30. Amethod for controlling unwanted vegetation which comprises allowing aherbicidally effective amount of at least one compound of claim 16 toact on plants, their seed and/or their habitat.
 31. The method of claim30 in which, in the compound of formula I, A is CR².
 32. The method ofclaim 30 in which, in the compound of formula I, R² is an optionallysubstituted five- or six-membered saturated, partially unsaturated oraromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selectedfrom the group consisting of O, N and S.
 33. The method of claim 30 inwhich, in the compound of formula I, R² is

in which # denotes the bond through which the group R² is attached and:R^(P2) is H or F; R^(P3) is H, F, Cl or OCH₃; and R^(P4) is H, F, Cl,CH₃, CF₃, OCH₃, OCH₂OCH₃ or OCH₂CH₂OCH₃.
 34. The method of claim 32 inwhich, in the compound of formula I, R² is an optionallyR^(b)-substituted heterocycle selected from the group consisting ofisoxazoline, tetrazolone, 1,2-dihydrotetrazolone,1,4-dihydrotetrazolone, tetrahydrofuran, dioxolane, piperidine,morpholine, piperazine, isoxazole, pyrazole, thiazole, oxazole, furyl,pyridine and pyrazine, and R^(b) is selected from the group consistingof C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyland C₁-C₄-alkylthio-C₁-C₄-alkyl.
 35. The method of claim 30 in which, inthe compound of formula I, R² is an aliphatic group selected from thegroup consisting of C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₂-C₄-alkoxy, C₂-C₄-haloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy,C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₄-alkoxycarbonyl,S(O)₂—C₁-C₈-alkyl and S(O)₂—C₁-C₈-haloalkyl.